Fungicidal cyclic amides

ABSTRACT

Cyclic amides of Formula I which are useful as fungicides: ##STR1## wherein A is N; G is N and the floating double bond is attached to A; W is O or S; X is OR 1 , S(O) m  R 1  or halogen; R 1 , R 2 , R 3 , R 4 , Y and Z are defined in the disclosure, are disclosed. Also, disclosed are fungicidal compositions containing these compounds and the use of these cyclic amide compounds for controlling plant diseases caused by fungal plant pathogens.

This application is a division of U.S. application Ser. No. 09/006,959filed Jan. 14, 1998, now pending which is a division of U.S. applicationSer. No. 08/640,884 filed May 8, 1996, now U.S. Pat. No. 5,747,516, thenational filing under 35 USC 371 of International Application No.PCT/US94/09525 filed Aug. 30, 1994, and a continuation-in-part of U.S.patent application Ser. No. 08/155,970 filed Nov. 19, 1993, nowabandoned, and U.S. patent application Ser. No. 08/155,963 filed Nov.19, 1993, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to cyclic amides substituted at the α-positionwith various aryl groups, their agriculturally suitable salts andcompositions, and methods of their use as general or selectivefungicides.

EP-A-398,692 discloses amides of Formula i as fungicides for cropprotection. Compounds of Formula i are: ##STR2## wherein

R¹ and R² are each hydrogen, lower alkyl, or lower cycloalkyl.

All the compounds disclosed in EP-A-398,692 have an aryl moiety bondedto an acyclic alkoxyiminoacetamide group. The cyclic amides of thepresent invention are not disclosed therein.

WO 93/07116 discloses compounds of Formula ii as fungicides for cropprotection. Compounds of Formula ii are: ##STR3## wherein

W is ##STR4##

Once again, the cyclic amides of this invention are not disclosedtherein.

J. heterocyclic Chem., (1987), 245, 465, J. Heterocyclic Chem., (1988),25, 130 and Australian J. Chem., (1977), 30 (8), 1815 disclose4-nitrophenyl isoxazoles (iii), phenyl pyrazolones (iv), and arylisothiazolinones (v) respectively. ##STR5##

However, no utility as fungicides is alleged and no ortho-substitutedcompounds of the present invention are disclosed.

SUMMARY OF THE INVENTION

This invention comprises compounds of Formula I including all geometricand stereoisomers, agriculturally suitable salts thereof, agriculturalcompositions containing them and their use as fungicides: ##STR6##wherein

A is O; S; N; NR⁵ ; or CR¹⁴ ;

G is C or N; provides that when G is C, A is O, S or NR⁵ and thefloating double bond is attached to G; and when G is N, A is N or CR¹⁴and the floating double bond is attached to A;

W is O or S;

X is OR¹ ; S(O)_(m) R¹ ; or halogen;

R¹, R², and R⁵ are each independently H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl;C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl;C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl, C₂ -C₄ alkoxycarbonyl; orbenzoyl optionally substituted with R¹³ ;

R³ and R⁴ are each independently H; halogen; cyano; nitro; C₁ -C₆ alkyl;C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂-C₆ haloalkynyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆ alkenyloxy; orC₂ -C₆ alkynyloxy;

Y is --O--; --S(O)_(n) --; --CHR⁶ CHR⁶ --; --CR⁶ ═CR⁶ --; --C.tbd.C--;--CHR⁶ O--; --OCHR⁶ --; --CHR⁶ S(O)_(n) --; --S(O)_(n) CHR⁶ --; --CHR⁶O--N═C(R⁷)--; --(R⁷)C═N--OCH(R⁶)--; --C(R⁷)═N--O--; --O--N═C(R⁷)--;--CHR⁶ OC(═O)N(R¹⁵)--; or a direct bond; and the directionality of the Ylinkage is defined such that the moiety depicted on the left side of thelinkage is bonded to the phenyl ring and the moiety on the right side ofthe linkage is bonded to Z;

R⁶ is independently H or C₁ -C₃ alkyl;

R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; C₂ -C₄alkoxycarbonyl; cyano; or morpholinyl;

Z is C₁ -C₁₀ alkyl, C₂ -C₁₀ alkenyl, or C₂ -C₁₀ alkynyl each optionallysubstituted with R⁸, or Z is C₃ -C₈ cycloalkyl or phenyl each optionallysubstituted with one of R⁹, R¹⁰, or both R⁹ and R¹⁰ ; or Z is a 3 to14-membered nonaromatic heterocyclic ring system selected from the groupmonocyclic ring, fused bicyclic ring and fused tricyclic ring, or Z is a5 to 14-membered aromatic heterocyclic ring system selected from thegroup monocyclic ring, fused bicyclic ring and fused tricyclic ring,each nonaromatic or aromatic ring system containing 1 to 6 heteroatomsindependently selected from the group 1-4 nitrogen, 1-2 oxygen, and 1-2sulfur, each nonaromatic or aromatic ring system optionally substitutedwith one of R⁹, R¹⁰, or both R⁹ and R¹⁰ ; or

R⁷ and Z are taken together to form CH₂ CH₂ CH₂, CH₂ CH₂ CH₂ CH₂, CH₂CH₂ OCH₂ CH₂, each CH₂ group optionally substituted with 1-2 halogen; or

Y and Z are taken together to form ##STR7##

R³, Y, and Z are taken together with the phenyl ring to form anaphthalene rin substituted on either ring with a floating R⁴ ; providedthat when R³, Y, Z are taken together with the phenyl ring to form anapthylene ring substituted by R⁴, and A is S, W is O, X is SCH₃ and R²is CH₃, then R other than H;

j is --CH₂ --; --CH₂ CH₂ --; --OCH₂ --; --CH₂ O--; --SCH₂ --; --CH₂ S--;--N(R¹⁶)CH₂ --; or --CH₂ N(R¹⁶)--; each CH₂ group optionally substitutedwith 1 to 2 CH₃ ;

R⁸ is 1-6 halogen; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆ alkylthio;C₁ -C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆ alkylsulfonyl; C₃ -C₆cycloalk C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆ alkyl); N(C₁-C₆ alkyl cyano; or nitro; or R⁸ is phenyl, phenoxy, pyridinyl,pyridinyloxy, thienyl furanyl, pyrimidinyl, or pyrimidinyloxy eachoptionally substituted with of R¹¹, R¹², or both R¹¹ and R¹² ;

R⁹ is 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₁ -C₆alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆alkylsulfonyl C₃ -C₆ cycloalkyl; C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆ alkyl);NH(C₁ -C₆ alky N(C₁ -C₆ alkyl)₂ ; --C(R¹⁸)═NOR¹⁷ ; cyano; or nitro; orR⁹ is phenyl, ben benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl,thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionallysubstituted with one of R R¹², or both R¹¹ and R¹² ;

R¹⁰ is halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁ -C₄ alkoxy; nitro; orcyano; or

R⁹ and R¹⁰, when attached to adjacent atoms, are taken together as--OCH₂ O----OCH₂ CH₂ O--; each CH₂ group optionally substituted with 1-2halogen;

R¹¹ and R¹² are each independently halogen; C₁ -C₄ alkyl; C₁ -C₄haloalkyl; C₁ -alkoxy; C₁ -C₄ haloalkoxy; nitro; or cyano;

R¹³ is halogen; C₁ -C₃ alkyl; C₁ -C₃ haloalkyl; C₁ -C₃ alkoxy; C₁ -C₃haloalkoxy; nitro; or cyano;

R¹⁴ is H; halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂-C₆ haloalke C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; or C₃ -C₆ cycloalkyl;

R¹⁵, R¹⁶, R¹⁷, and R¹⁸ are each independently H; C₁ -C₃ alkyl; or phenyloptionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano;

m, n and q are each independently 0, 1 or 2; and

p and r are each independently 0 or 1.

In the above recitations, the term "alkyl", used either alone or incompound words such as "haloalkyl" denotes straight-chain or branchedalkyl; e.g., methyl, ethyl, n-propyl, i-propyl, or the different butyl,pentyl or hexyl isomers. "Alkenyl" denotes straight-chain or branchedalkenes; e.g., 1-propenyl, 2-propenyl, and the different butenyl,pentenyl and hexenyl isomers. "Alkenyl" also denotes polyenes such as1,3-hexadiene. "Alkynyl" denotes straight-chain or branched alkynes;e.g., ethynyl, 1-propynyl, 3-propynyl and the different butynyl,pentynyl and hexynyl isomers. "Alkynyl" can also denote moietiescomprised of multiple triple bonds; e.g., 2,4-hexadiyne. "Alkoxy"denotes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and thedifferent butoxy, pentoxy and hexyloxy isomers. "Alkenyloxy" denotesstraight-chain or branched alkenyloxy moieties. Examples of alkenyloxyinclude H₂ C═CHCH₂ O, (CH₃)₂ C═CHCH₂ O, (CH₃)CH═CHCH₂ O,(CH₃)CH═C(CH₃)CH₂ O and CH₂ ═CHCH₂ CH₂ O. "Alkynyloxy" denotesstraight-chain or branched alkynyloxy moieties. Examples includeHC.tbd.CCH₂ O, CH₃ C.tbd.CCH₂ O and CH₃ C.tbd.CCH₂ CH₂ O. The term"halogen", either alone or in compound words such as "haloalkyl",denotes fluorine, chlorine, bromine or iodine. Further, when used incompound words such as "haloalkyl", said alkyl may be partially or fullysubstituted with halogen atoms which may be the same or different.Examples of "haloalkyl" include F₃ C, ClCH₂, CF₃ CH₂ and CF₃ CCl₂. Theterm "cycloalkyl" denotes cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl moieties. The term "nonaromatic heterocyclic ring system"includes fully saturated heterocycles and partially aromaticheterocycles. The total number of carbon atoms in a substituent group isindicated by the "C_(i) -C_(j) " prefix where i and j are numbers from 1to 10. For example, C₁ -C₃ alkyl designates methyl through propyl; C₂alkoxy designates CH₃ CH₂ O; and C₃ alkoxy designates, for example, CH₃CH₂ CH₂ O or (CH₃)₂ CHO. In the above recitations, when a compound ofFormula I is comprised of one or more aromatic nitrogen-containing rings(e.g., pyridinyl and pyrimidinyl), all bonds to these heterocycles aremade through the carbon atom(s) of the moieties.

Preferred compounds, compositions containing them, and methods of theiruse for reasons of better activity and/or ease of synthesis are:

Preferred 1. Compounds of Formula I above wherein:

W is O;

R¹ is C₁ -C₃ alkyl or C₁ -C₃ haloalkyl;

R² is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; or C₃ -C₆ cycloalkyl;

R³ and R⁴ are each independently H; halogen; cyano; nitro; C₁ -C₆ alkyl;C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; or C₁ -C₆ haloalkoxy;

Y is --O--; --CH═CH--; --CH₂ O--; --OCH₂ --; --CH₂ S(O)_(n) --; --CH₂O--N═C(R⁷)--; --C(R⁷)═N--O--; --CH₂ OC(O)NH--; or a direct bond;

R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ alkynyl;or cyano;

Z is C₁ -C₁₀ alkyl optionally substituted with R⁸ ; or C₃ -C₈ cycloalkylor phenyl, each optionally substituted with one of R⁹, R¹⁰, or both R⁹and R¹⁰ ; or Z is ##STR8## each group optionally substituted with oneR⁹, R¹⁰, or both R⁹ and R¹⁰ ; or

R³, Y, and Z are taken together with the phenyl ring to form anaphthalene ring substituted on either ring with a floating R⁴ ; or

Y and Z are taken together to form ##STR9## R⁸ is 1-6 halogen; C₁ -C₆alkoxy; C₁ -C₆ haloalkoxy; or R⁸ is pehnyl, phenoxy, pyridinyl,pyridinyloxy, pyrimidinyl, or pyrimidinyloxy each optionally substitutedwith one of R¹¹, R¹², or both R¹¹ and R¹² ;

R⁹ is 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆haloalkoxy; C₁ -C₆ alkylthio; cyano; CO₂ (C₁ -C₆ falkyl); NH(C₁ -C₆alkyl); or N(C₁ -C₆ alkyl)₂ ; or R⁹ is C₃ -C₆ cycloalkyl, pyhenyl,phenoxy, pyridinyl, pyridinyloxy, pyrimidinyl, or pyrimidinyloxy eachoptionally substituted with one of R¹¹, R¹², or both R¹¹ and R¹² ; and

R¹⁹ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; or phenyl optionallysubstituted with halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy,C₁ -C₄ haloalkoxy, nitro or cyano.

Preferred 2. Compounds of Preferred 1 wherein:

Z is phenyl or Z-1 to Z-21, each optionally substituted with one of R⁹,R¹⁰, or both R⁹ and R¹⁰ ; or

Y and Z are taken together to form ##STR10## J is --CH₂ -- or --CH₂ CH₂--; p is 0; and

r is 1.

Preferred 3. Compounds of Preferred 2 wherein:

A is O; N; NR⁵ ; or CR¹⁴ ;

X is OR¹ ;

R¹ is C₁ -C₃ alkyl;

R² is H or C₁ -C₂ alkyl;

R³ and R⁴ are each h;

Y is --O--; --CH═CH--; --CH₂ O--; --OCH₂ --; --CH₂ O--N═C(R⁷)--; or--CH₂ OC(═O)NH--;

R⁷ is H; C₁ -C₃ alkyl; or C₁ -C₃ haloalkyl; and

Z is phenyl, pyridinyl, pyrimidinyl, or thienyl, each optionallysubstituted with one of R⁹, R¹⁰, or both R⁹ and R¹⁰.

Preferred 4. Compounds of Preferred 3 wherein:

A is O or NR⁵ ;

G is C;

Y is --O--; --CH₂ O--; --OCH₂ --; or --CH₂ O--N═C(R⁷)--; and

R⁷ is H; C₁ -C₂ alkyl; or C₁ -C₂ haloalkyl.

Preferred 5. Compounds of Preferred 3 wherein:

A is N or CR¹⁴ ;

G is N;

Y is --O--; --CH₂ O--; --OCH₂ --; or --CH₂ O--N═C(R⁷)--; and

R⁷ is H; C₁ -C₂ alkyl; or C₁ -C₂ haloalkyl.

Preferred 6. Compounds of Preferred 4 wherein:

R¹ is methyl;

R² is methyl; and

Z is phenyl optionally substituted with one of R⁹, R¹⁰, or both R⁹ andR¹⁰.

Preferred 7. Compounds of Preferred 5 wherein:

R¹ is methyl;

R² is methyl; and

Z is phenyl optionally substituted with one of R⁹, R¹⁰, or both R⁹ andR¹⁰.

It is recognized that some reagents and reaction conditions describedbelow for preparing compounds of Formula I may not be compatible withsome functionalities claimed for R¹, R², R³, R⁴, A, G, W, X, Y, and Z.In these cases, the incorporation of protection/deprotection sequencesinto the synthesis may be necessary in order to obtain the desiredproducts. The cases in which protecting groups are necessary, and whichprotecting group to use, will be apparent to one skilled in chemicalsynthesis.

In the following description of the preparation of compounds of FormulaI, compounds denoted as Formula Ia through Ik are various subsets of thecompounds of Formula I. All substituents for compounds of Formula Iathrough Ik and Formulae 1-39 are as defined above for Formula I exceptwhere indicated otherwise.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers and geometricisomers. One skilled in the art will appreciate that one stereoisomermay be more active than the others and how to separate saidstereoisomers. Accordingly, the present invention comprises mixtures,individual stereoisomers, and optically active mixtures of compounds ofFormula I as well as agriculturally suitable salts thereof.

One skilled in the art will recognize that some compounds of Formula Ican exist in one or more tautomeric forms. For example, a compound ofFormula I wherein R² is H may exist as tautomer Ia or Ib, or both Ia andIb. The present invention comprises all tautomeric forms of compounds ofFormula I. ##STR11##

DETAILED DESCRIPTION OF THE INVENTION

The compounds of Formula I can be prepared as described below inProcedures 1) to 5). Procedures 1) to 4) describe syntheses involvingconstruction of the amide ring after the formation of the aryl moiety.Procedure 5) describes syntheses of aryl moiety with the amide ringalready in place.

1) Alkylation Procedures

The compounds of Formula I are prepared by treating compounds of Formulawith an appropriate alkyl transfer reagent in an inert solvent with orwithout addition acidic or basic reagents or other reagents (Scheme 1).Suitable solvents are selected from the group consisting of polaraprotic solvents such as acetonitrile, dimethylformamide ordimethylsulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, ordiethyl ether, ketones such as acetone or 2-butanone; hydrocarbons suchas toluene or benzene; and halocarbons such as dichloromethane orchloroform. ##STR12##

For example, compounds of Formula I can be prepared by the action ofdiazoalkane reagents of Formula 2 such as diazomethane (Q=H) ortrimethylsilydiazomethane (Q=(CH₃)₃ Si) on compounds of dicarbonylcompounds or Formula 1 (Method 1). Use of trimethylsilyldiazomethanerequires a protic cosolvent such as methanol. For examples of theseprocedures, see Chem. Pharm. Bull., (1984), 32, 3759.

As indicated in Method 2, compounds of Formula I can also be prepared bycontacting carbonyl compounds of Formula 1 with alkyltrichloroacetimidates of Formula 3 and a Lewis acid catalyst. SuitableLewis acids include trimethylsilyl triflate and tetrafluoroboric acid.The alkyl trichloroacetimidates can be prepared from the appropriatealcohol and trichloroacetonitrile as described in the literature (J.Danklmaier and H. Honig, Synth. Commun., (1990), 20, 203).

Compounds of Formula I can also be prepared from compounds of Formula 1by treatment with a trialkyloxonium tetrafluoroborate (i.e., Meerwein'ssalt) of Formula 4 (Method 3). The use of trialkyloxonium salts aspowerful alkylating agents is well known in the art (see U. Schollkopf,U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl., (1981), 20, 798).

Other alkylating agents which can convert carbonyl compounds of Formula1 to compounds of Formula I are dialkyl sulfates such as dimethylsulfate, haloalkyl sulfonates such as methyl trifluoromethanesulfonate,and alky halides such as iodomethane and propargyl bromide (Method 4).These alkylations can be conducted with or without additional base.Appropriate bases include alkali metal alkoxides such as potassiumtert-butoxide, inorganic bases such as sodium hydride and potassiumcarbonate, or tertiary amines such as triethylamine, pyridine,1,8-diazabicyclo[5.40]undec-7-ene (DBU), and triethylenediamine. See R.E. Benson, T. L. Cairns, J. Am. Chem. Soc., (1948), 70, 2115 foralkylation examples using agents of this type.

Compounds of Formula 1a (compounds of Formula 1 wherein G=C, W=O andX=OH) can be prepared by condensation of malonates or malonatederivatives of Formula 5 with an ambident nucleophile of Formula 6(Scheme 2). The nucleophiles of Formula 6 are N-substitutedhydroxylamines (HO--NHR²) and substituted hydrazines (HN(R⁵)--NHR²).Examples of such nucleophiles are N-methylhydroxylamine andmethylhydrazine. The preparation of the malonate esters of Formula 5 canbe prepared by methods described hereinafter. The esters of Formula 5can also be activated by first hydrolyzing the ester to form thecorresponding carboxylic acid, and then converting the acid into theacid chloride (T=Cl) using thionyl chloride or oxalyl chloride, or intothe acyl imidazole (T=1-imidazolyl) by treating with1,1'-carbonyldiimidazole. ##STR13##

Esters of Formula 5a can be prepared from copper (I)-catalyzed reactionof malonate esters of Formula 7 with substituted iodobenzenes of Formula8 according methods adapted from A. Osuka, T. Kobayashi and H. Suzuki,Synthesis, (1983), 67, and illustrated in Scheme 3. ##STR14##

Additionally, the malonate esters of Formula 5a can be prepared bytreating phenyl acetic acid esters of Formula 9 with a dialkyl carbonateor alkyl chloroformate in the presence of a suitable base sucy as, butnot limited to, sodium metal and sodium hydride (Scheme 4). For example,see J. Am. Chem. Soc., (1928), 50, 2758. ##STR15##

Esters of Formula 9 can be prepared from acid-catalyzed alcoholysis ofphenyl acetonitriles of Formula 10 or esterification of phenyl aceticacids of Formula 11 as illustrated in Scheme 5 (see Org. Synth., Coll.Vol. I, (1941), 270). ##STR16##

Phenyl acetic acid esters of Formula 9a can also be prepared by copper(I)-catalyzed condensation of phenyl halides of Formula 12 withcompounds of Formula 13 as described in EP-A-307,103 and illustratedbelow in Scheme 6. ##STR17##

Some esters of Formula 9 (Formula 9b) can also be prepared by formingthe Y² bridge using conventional nucleophilic substitution chemistry(Scheme 7). Displacement of an appropriate leaving group (Lg) inelectrophiles of Formula 15 or 16 with a nucleophilic ester of Formula14 affords compounds of Formula 9b. A base, for example sodium hydride,is used to generate the corresponding alkoxide or thioalkoxide of thecompound of Formula 14. ##STR18##

Some esters of Formula 9 (Formula 9e) can also be prepared by formingthe Y.sup. bridge from substituted hydroxylamine 9d and carbonylcompounds 14a. The hydroxylamine 9d is in turn prepared from esters 9c.This method has been described in EP-600,835 and illustrated in Scheme8. ##STR19##

2) Displacement and Conjugate Addition/Elimination Procedures

Compounds of Formula I can also be prepared by reaction of Formula 17compounds with alkali metal alkoxides (R¹ O⁻ M⁺) or alkali metalthioalkoxides (R¹ S⁻ M⁺) in a suitable solvent (Scheme 9). The leavinggroup Lg¹ in the amides of Formula 17 are any group known in the art toundergo a displacement reaction of this type. Examples of suitableleaving groups include chlorine, bromine, and sulfonyl and sulfonategroups. Examples of suitable inert solvents are dimethylformamide ordimethylsulfoxide. ##STR20##

Compounds of Formula 17a can be prepared from compounds of Formula 1b(compounds of Formula 1 wherein X is OH) by reaction with halogenatingagents such as thionyl chloride or phosphorus oxybromide to form thecorresponding β-halo-substituted derivatives (Scheme 10). Alternatively,compounds of Formula 1b can be treated with alkylsulfonyl halide orhaloalkylsulfonyl anhydride, such as methane sulfonyl chloride,p-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, toform the corresponding β-alkylsulfonate of Formula 17a. The reactionwith the sulfonyl halides may be performed in the presence of a suitablebase (e.g., triethylamine). ##STR21##

As illustrated in Scheme 11, sulfonyl compounds of Formula 17b can beprepared by oxidation of the corresponding thio compound of Formula 18using well-known methods for the oxidation of sulfur (see Schrenk, K. InThe Chemistry of Sulphones and Sulphoxides; Patai, S. et al., Eds.;Wiley: New York, 1988). Suitable oxidizing reagents includemeta-chloro-peroxybenzoic acid, hydrogen peroxide and Oxone® (KHSO₅ ).##STR22##

Alternatively, halo-compounds of Formula 17c (compounds of Formula 17awherein A=N, G=N, and W=O) can be prepared from hydrazides of Formula 19as illustrated in Scheme 12. When R²² =C(=S)S(C₁ -C₄ alkyl), the diacylcompound of Formula 19 is treated with excess thionyl halide, forexample excess thionyl chloride. The product formed first is thering-closed compound of Formula 20 which can be isolated or converted insitu to the compound of Formula 17c; see P. Molina, A. Tarraga, A.Espinosa, Synthesis, (1989), 923 for a description of this process.

Alternatively, when R²² =R² as defined above, the hydrazide of Formula19 is cyclized with phosgene to form the cyclic urea of Formula 17cwherein hal=Cl. This procedure is described in detail in J. Org. Chem.,(1989), 54, 1048. ##STR23##

The hydrazides of Formula 19 can be prepared as illustrated in Scheme13. Condensation of the isocyanate of Formula 21 with the hydrazine ofFormula H₂ NNR² R²² in an inert solvent such as tetrahydrofuran affordsthe hydrazide. ##STR24##

3) Conjugate Addition/Cyclization Procedures

In addition to the methods disclosed above, compounds of Formula Iwherein X=SR¹ and G=C (Formula Ic) can be prepared by treating aketenedithioacetal of Formula 22 with an ambident nucleophile of Formula6 (Scheme 14). The nucleophiles of Formula 6 are described above.##STR25##

Ketene dithioacetals of Formula 22a can be prepared by condensing phenylacetic acid esters of Formula 9 with carbon disulfide in the presence ofa suitable base, followed by reaction with two equivalents of an R¹-halide, such as iodomethane or propargyl bromide (Scheme 15). ##STR26##

Compounds of Formula 1a (compounds of Formula 1 wherein A=N, G=N) can beprepared by condensation of N-amino-ureas of Formula 23 with acarbonylating agent of Formula 24 (Scheme 16). The carbonylating agentsof Formula 24 are carbonyl or thiocarbonyl transfer reagents such asphosgene, thiophosgene, diphosgene (ClC(═O)OCCl₃), triphosgene (Cl₃COC(═O)OCCl₃), N,N'-carbonyldiimidazole, N,N'-thiocarbonyldiimidazole,and 1,1'-carbonyldi(1,2,4-triazole). Alternatively, the compounds ofFormula 24 can be alkyl chloroformates or dialkyl carbonates. Some ofthese carbonylating reactions may require the addition of a base toeffect reaction. Appropriate bases include alkali metal alkoxides suchas potassium tert-butoxide, inorganic bases such as sodium hydride andpotassium carbonate, or tertiary amines such as triethylamine, pyridine,1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or triethylenediamine.Suitable solvents include polar aprotic solvents such as acetonitrile,dimethylformamide, or dimethylsulfoxide; ethers such as tetrahydrofuran,dimethoxyethane, or diethyl ether, ketones such as acetone or2-butanone; hydrocarbons such as toluene or benzene; or halocarbons suchas dichloromethane or chloroform. The reaction temperature can varybetween 0° C. and 150° C. and the reaction time can be from 1 to 72hours depending on the choice of base, solvent, temperature, andsubstrates. ##STR27##

N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17.Treatment of an aniline of Formula 25 with phosgene, thiophosgene,N,N'-carbonyldiimidazole, or N,N'-thiocarbonyldiimidazole produces theisocyanate or isothiocyanate of Formula 26. A base can be added forreactions with phosgene or thiophosgene. Subsequent treatment of theiso(thio)cyanate with an R² -substituted hydrazine produces theN-amino-urea of Formula 23. ##STR28##

Compounds of Formula 1b (compounds of Formula 1 wherein A=CR⁵, G=N, andX=O) can be prepared by either method illustrated in Scheme 18. Ureas ofFormula 27 are reacted with activated 2-halocarboxylic acid derivativessuch as 2-halocarboxylic acid chlorides, 2-halocarboxylic acid esters or2-haloacyl imidazoles. The initial acylation on the aniline nitrogen isfollowed by an intramolecular displacement of the 2-halo group to effectcyclization. Base may be added to accelerate the acylation and/or thesubsequent cyclization. Suitable bases include triethylamine and sodiumhydride. Alternatively, Formula 1b compounds can be prepared by reactionof Formula 26 isocyanates with Formula 28a esters. As described above,base may be added to accelerate the reaction and subsequent cyclizationto Formula 1b compounds. ##STR29##

The ureas of Formula 27 can be prepared by either of the methodsillustrated in Scheme 19. The anilines of Formula 25 can be contactedwith an isocyanate or isothiocyanate of Formula R² N═C═W as describedabove. Alternatively, an isocyanate or isothiocyanate of Formula 26 canbe condensed with an amine of Formula R² -NH₂ to form the urea. Theanilines and iso(thio)cyanates of Formulae 25 and 26, respectively, arecommercially available or prepared by well-known methods. For example,isothiocyanates can be prepared by methods described in J. Heterocycl.Chem., (1990), 27, 407. Isocyanates can be prepared as described inMarch, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York,(1985), pp 944, 1166. ##STR30##

4) Thionation Procedures

Compounds of Formula Ie, compounds of Formula I wherein W=S, can beprepared by treating compounds of Formula Id (I wherein W=O) withthionating reagents such as P₂ S₅ or Lawesson's reagent[2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4 - diphosphetane-2,4-disulfide]as illustrated in Scheme 20 (see Bull. Soc. Chim. Belg., (1978), 87,229; and Tetrahedron Lett., (1983), 24, 3815). ##STR31##

5) Aryl Moiety Synthesis Procedures

Compounds of Formula If (compounds of Formula I wherein Y is CHR⁶ O,CHR⁶ S, or CHR⁶ O--N═CR⁷) can be prepared by contacting benzyl halidesof Formula 29 with various nucleophiles (Scheme 21). The appropriatealcohol or thiol is treated with a base, for example sodium hydride, toform the corresponding alkoxide or thioalkoxide which acts as thenucleophile. ##STR32##

Benzyl halides of Formula 29 can be prepared by radical halogenation ofthe corresponding alkyl compound (i.e., H instead of halogen in Formula29), or by acidic cleavage of the corresponding methylether (i.e., OMeinstead of halogen in Formula 29).

Compounds of Formula I wherein Y is CR⁶ ═CR⁶ and CHR⁶ --CHR⁶ (Formula Igand Ih, respectively) can be prepared as illustrated in Scheme 22.Treatment of the benzyl halides of Formula 29 with triphenylphosphine ora trialkylphosphite produces the corresponding phosphonium salt (Formula30) or phosphonate (Formula 31), respectively. Condensation of thephosphorus compound with a base and a carbonyl compound of FormulaZ(R⁶)C═O affords the olefin of Formula Ig. ##STR33##

The olefins of Formula Ig can be converted to the saturated compounds ofFormula Ih by hydrogenation over a metal catalyst such palladium oncarbon as is well-known in the art (Rylander, Catalytic Hydrogenation inOrganic Synthesis; Academic: New York, 1979).

Formula Ii alkynes can be prepared by halogenation/dehalogenation ofFormula Ig olefins using procedures well-known in the art (March, J.Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p924). Additionally, Formula Ii alkynes can be prepared by well-knownreaction of aromatic halides with alkyne derivatives in the presence ofcatalysts such as nickel or palladium (see J. Organomet. Chem., (1975),93 253-257).

The olefin of Formula Ig can also be prepared by reversing thereactivity of the reactants in the Wittig or horner-Emmons condensation.For example, 2-alkylphenyl derivatives of Formula 31 can be convertedinto the corresponding dibromo-compound of Formula 33 as illustrated inScheme 23 (see Synthesis, (1988), 330). The dibromo-compound can behydrolyzed to the carbonyl compound of Formula 34, which in turn can becondensed with phyosphorus-containing nucleophile of Formula 35 or 36 toafford the olefin of Formula Ig. ##STR34##

Oximes of Formula Ij (Formula I wherein Y is C(R⁷)═N--O) can be preparedfrom carbonyl compounds of Formula 37 by condensation withhydroxylamine, followed by O-alkylation with electrophiles of FormulaZ--(Cl, Br, or I) (Scheme 24). Alternatively, the O-substitutedhydroxylamine can be condensed with the carbonyl compound of Formula 37to yield oximes of Formula Ij directly. ##STR35##

Carbamates of Formula Ik can be prepared by reacting benzyl alcohols ofFormula 38 with isocyanates of Formula 39 (Scheme 25). A base such astriethylamine can be added to catalyze the reaction. ##STR36##

The following Examples are representative of the production of the novelcyclic amides of Formula I. ¹ H NMR Spectra are reported in ppmdownfield from tetramethylsilane; s=singlet, d=doublet, t=triplet,dt=doublet of triplets, td=triplet of doublets, m=multiplet.

EXAMPLE 1 Step A

Preparation of Methyl 2-(3-methoxyphenoxy)phenylacetate

(2-Chlorophenyl)acetic acid (60 g), 3-methoxyphenol (87 g), potassiumcarbonate (97.2 g) and copper (I) chloride (0.6 g) were combined andmechanically stirred to give a thick brown suspension. The suspensionwas heated for 4.5 h, then cooled to 70° C. and 10 mL ofN,N-dimethylformamide was added. The mixture was poured into ice waterand acidified with concentrated aqueous HCl. The mixture was extractedwith diethyl ether and the combined extracts were washed with water (4times) dried (MgSO₄), filtered and concentrated under reduced pressureto provide 122 g of an oil. The crude material was dissolved in 73 mL ofmethanol and then 2.1 mL of concentrated sulfuric acid was added. Themixture was heated at reflux for 4 h. The mixture was poured into icewater and extracted with diethyl ether. The combined organic phases werewashed with 10% aqueous NaOH solution (2 times), then water (4 times),then brine. The organic phase was dried (MgSO₄), filtered andconcentrated under reduced pressure to yield 46.4 g (48%) of the titlematerial of Step A as a reddish oil. ¹ H NMR (CDCl₃): δ 6.45-7.4 (m,8H),3.76 (s,3H), 3.69 (s,2H), 3.62 (s,3H).

Step B

Preparation of Dimethyl [2-(3-methoxyphenoxy)phenyl]propanedioate

Methyl 2-(3-methoxyphenoxy) phenylacetate (6.81 g) was dissolved in 11mL of dimethyl carbonate and 600 mg of sodium was added. The mixture washeated at reflux for 10 h, then cooled. The reaction mixture wasquenched with water, acidified with concentrated aqueous HCl andextracted with dichloromethane. The combined organic extracts were dried(MgSO₄), filtered and concentrated under reduced pressure to give anoil. The desired material was separated from unreacted starting materialby flash chromatography (4:1 hexane: ethyl acetate as eluant) to yieldafter concentration, 3.54 g (43%) of the title compound of Step B. ¹ HNMR (CDCl₃): δ 7.46 (dd,J=1.5,7.5 Hz,1H), 7.29 (t,J=8 Hz,1H), 7.2(m,2H), 6.92 (d,J=8 Hz,1H), 6.65 (td,J=1.5,7.5 Hz,1H), 6.5 (m,2H), 5.14(s,1H), 3.77 (s,3H), 3.73 (s,6H).

Step C

Preparation of5-Hydroxy-4-[2-(3-methoxyphenoxy)phenyl]-2-methyl-3(2H)-isoxazolone

N-Methylhydroxylamine hydrochloride (2.79 g) was dissolved in 20 mL ofmethanol at reflux. The solution was cooled and treated with a solutionof 3.76 g potassium hydroxide in 15 mL of methanol. The precipitatedpotassium chloride was removed by filtration and a solution of 3.54 g ofdimethyl [2-(3-methoxyphenoxy)-phenyl]propanedioate in 25 mL of methanolwas added dropwise. The mixture was stirred at room temperatureovernight. The reaction mixture was concentrated under vacuum to avolume of about 30 mL and acidified with concentrated aqueous HCl, withcooling. The solvents were removed under reduced pressure and theresidue was partitioned between water and dichloromethane. The combinedorganic phases were dried (MgSO₄), filtered and concentrated underreduced pressure to yield 2.95 g (88%) of the title compound of Step C.¹ H NMR (CDCl₃): δ 7.2-7.4 (m,3H), 7.12 (dt,J=1,7.5 Hz,1H), 6.81(d,J=8.5 Hz,1H), 6.72 (d,J=8 Hz,1H), 6.6 (m,2H), 4.43(s,1H), 3.77(s,3H), 3.28 (s,3H).

Step D

Preparation of5-Methoxy-4-[2-(3-methoxyphenoxy)phenyl]-2-methyl-3(2H)-isoxazolone

5-Hydroxy-4-[2-(3-methoxyphenoxy)phenyl]-2-methyl-3(2H)-isoxazolone (2.5g) was dissolved in 3 mL of methanol and 15 mL of toluene and cooled inan icebath. Trimethylsilyldiazomethane (5 mL of a 2.0 M solution inhexane) was added dropwise. Gas evolution was observed. The resultingyellow solution was stirred at room temperature overnight. The solventswere removed under reduced pressure and the residue was purified byflash chromatography (1:1 hexane:ethyl acetate as eluant). The secondeluting component was collected to yield 950 mg (36%) of the titlecompound of Step D. ¹ H NMR (CDCl₃): δ 7.51 (dd,J=1.7, 7.5 Hz,1H), 7.27(dt,J=1.7, 7.5 Hz,1H). 7.17 (m,2H), 6.97 (dd,J=1, 8 Hz,1H), 6.5 (m,3H),3.92 (s,3H), 3.74 (s,3H), 3.33 (s,3H).

EXAMPLE 2 Step A

Preparation of 1-(Bromomethyl)-2-iodobenzene

To a solution of 2-iodobenzyl alcohol (50 g) in diethyl ether (500 mL),cooled in an ice-water bath, was added dropwise phosphorus tribromide(28 mL). The reaction mixture was chilled in a refrigerator for 3.5 h,then quenched by slow addition of methanol (50 mL). The mixture waswashed with water, then saturated sodium bicarbonate, then water (100 mLeach). The organic phase was dried (MgSO₄), filtered and concentratedunder reduced pressure to a white solid, which was triturated in hexaneand collected by filtration to yield 58 g (91%) of the title material ofStep A as a solid, mp 55-57° C.

Step B

Preparation of 1-Iodo-2-[(2-methylphenoxy)methyl]benzene

Sodium hydride (60% oil dispersion) (7.8 g) was added portionwise to aice-water cooled solution of o-cresol (21.1 g) in tetrahydrofuran (500mL). The mixture was stirred 20 minutes and then1-(bromomethyl)-2-iodobenzene (58 g) was added. The mixture was warmedto 60° C. for 16 h. Additional sodium hydride (2 g) was added and thereaction mixture heated for an additional 3 h. The reaction mixture wascooled and carefully quenched with water and extracted with ethylacetate (2×250 mL). The combined organic extracts were dried (MgSO₄),filtered and concentrated under reduced pressure to an oil, which wastriturated with cold hexane to provide a solid which was collected byfiltration to yield 59.1 g (94%) of the title compound of Step B as awhite solid, mp 106-108° C.

Step C

Preparation of Dimethyl [2-[(2-methylphenoxy)methyl]phenyl]propanedioate

To a suspension of sodium hydride (60% oil dispersion) (15.4 g) in 90 mLof 1,3-dimethyl-3,4,5,6-tetrahydro-2 [1H]-pyrimidinone (DMPU), cooled inan ice-water bath, was added dropwise a solution of dimethyl malonate(44 mL) in DMPU (150 mL). The mixture was stirred 20 minutes after theaddition was completed, and then 1-iodo-2-[(2-methylphenoxy)methyl]benzene (62.5 g) and cuprous iodide (73.3 g)were added. The resulting mixture was stirred at 100° C. for 5 h, thenstirred at 25° C. overnight. The mixture was diluted with 1 N, HCl (˜150mL) and extracted with diethyl ether (3×400 mL). The combined organicextracts were dried (MgSO₄), filtered and concentrated under reducedpressure to a semi-solid, which was purified by flash chromatography onsilica gel (5:2 hexane: ethyl acetate as eluant). The major material wascollected and concentrated to a white solid, which was triturated inhexane and collected by filtration to yield 56.9 g (79%) of the titlecompound of Step C as a white solid, mp 99-103° C.

Step D

Preparation of5-Hydroxy-4-[2-[(2-methylphenoxy)methyl]phenyl]-3(2H)-isoxazolone

To a solution of N-methylhydroxylamine hydrochloride (34.7 g) inmethanol (120 mL), cooled in an ice-water beth, was added dropwise asolution of potassium hydroxide (46.6 g) in methanol (80 mL). After theaddition was complete, the mixture was stirred 10 minutes. The potassiumchloride precipitate was removed by filtration and a solution ofdimethyl [2-[(2-methylphenoxy)methyl]phenyl]propanedioate (44 g) in 100mL of methanol was added to the N-methyl-hydroxylamine solution. Themixture was stirred for 3 days and then cooled in an ice-water bath.Concentrated HCl (15 mL) was added and the solid was removed byfiltration. The solvent was removed under vacuum and the residue dilutedwith ˜100 mL of water and then extracted with dichloromethane (3×150mL), then ethyl acetate (3×100 mL). The combined organic extracts weredried (Mg SO₄), filtered and concentrated under reduced pressure toyield 31.3 g (75%) of the title compound of Step D as a semi-solid. ¹ HNMR (DMSO-d₆): δ 7.4 (m,2H), 7.15 (m,2H), 7.10 (m,2H), 6.8 (m,2H), 5.16(s,2H), 2.9 (s,3H), 2.23 (s,3H).

Step E

Preparation of5-Methoxy-2-methyl-4-[2-[(2-methylphenoxy)methyl]phenyl]-3(2H)-isoxazolone

5-Hydroxy-4-[2-[(2-methylphenoxy)methyl]phenyl]-3(2H)-isoxazolone (31.3g) was dissolved in 330 mL of 10:1 toluene:methanol and cooled in anice-water bath. Trimethylsilyl-diazomethane (˜2M in hexane) (55 mL) wasadded dropwise. Gas evolution was observed. The yellow solution wasstirred at 25° C. for 2 h. The solution was diluted with 100 mL of waterand extracted with ethyl acetate (4×100 mL). The combined organicextracts were dried (Mg SO₄), filtered and concentrated under reducedpressure to yield an oil, which was purified by flash chromatography(silica gel; 1:1 hexane:ethyl acetate as eluant). The second elutingcomponent was collected to yield 4.35 g (13%) of the title compound ofStep E as a white solid, mp 90-92° C. ¹ H NMR (CDCl₃) δ 7.61(d,1H),7.35(m,3H), 7.12(m,2H), 6.84(m,2H), 5.12(s,2H), 3.96(s,3H), 3.41(s,3H),2.24(s, 3H).

EXAMPLE 3 Step A

Preparation of 1-Methyl-N-(2-phenoxyphenyl)hydrazinecarboxamide

2-Phenoxyaniline (5.57 g) and triethylamine (4.2 mL) were dissolved in100 mL of 1,2-dichloroethane. Triphosgene (Cl₃ COC(═O)OCCl₃, 2.97 g) wasadded and a precipitate formed. The mixture was heated to reflux and thesolid redissolved. After 5.5 h, the solution was cooled and 1.6 mL ofmethyl hydrazine was added and a new precipitate formed. The mixture wasstirred at room temperature overnight. The solvent was removed and theresidue was partitioned between ethyl acetate and 1N aqueous HClsolution. The organic phases were dried (MgSO₄), filtered, andconcentrated under reduced pressure. The residue was purified by flashchromatography (1:1 hexane:ethyl acetate as eluant). The second-leastpolar component was collected, the eluant was removed under reducedpressure, and the residue was triturated with hexane to afford 3.86 g(50%) of the title compound of Step A, m.p. 117-119° C.

Step B

Preparation of2-Methyl-4-(2-phenoxyphenyl)-5-thioxo-1,2,4-triazolidin-3-one

A solution of 1.54 g of 1-methyl-N-(2-phenoxyphenyl)hydrazinecarboxamidein 50 mL of tetrahydrofuran, cooled in an ice bath, was treated with0.46 mL of thiophosgene, and then 1.68 mL of triethylamine. Aprecipitate formed and the mixture was stirred at ambient temperatureovernight. The precipitate was removed by filtration and washed withtetrahydrofuran. The combined filtrate and washings were concentratedunder reduced pressure to afford 1.8 g of an amber glassy oil. The crudematerial was used in the next step without further purification. ¹ H NMR(CDCl₃): δ 6.8-7.4 (m, 9H), 3.57 (s,3H).

Step C

Preparation of2,4-Dihydro-2-methyl-5-(methylthio)-4-(2-phenoxyphenyl)-3H-1,2,4-triazol-3-one

A solution of 900 mg of crude2-methyl-4-(2-phenoxyphenyl)-5-thioxo-1,2,4-triazolidin-3-one in 50 mLof tetrahydrofuran was treated with 150 mg of sodium hydride (60% oildispersion). After 5 minutes, 0.5 mL of iodomethane was added, and themixture was stirred at ambient temperature overnight. The solid wasremoved by filtration and the filtrate concentrated to an oil. The oilwas partitioned between ether and 1N hydrochloric acid solution. Theorganic phases were dried (MgSO₄), filtered and concentrated underreduced pressure. The residue was triturated in hexane/n-butyl chlorideto afford 530 mg (56%) of the title compound of Step C, m.p. 129-130° C.

EXAMPLE 4 Step A

Preparation of 2,2-Dimethyl-N-(2-methylphenyl) hydrazine carboxamide

o-Tolyl isocyanate (10.0 g) was dissolved in 75 mL toluene under N₂. Thesolution was cooled to 5° C. and to this was slowly added a solution intoluene of 1,1-dimethylhydrazine (5.7 mL). After addition, the ice-bathwas removed and the resulting slurry allowed to stir an additional 10minutes. The solid was filtered off rinsing successively with hexane, asmall amount of 20% diethylether/hexane, then hexanes again. Thisafforded 11.1 g (77%) of the title compound of Step A. ¹ H NMR (CDCl₃) δ8.1 (bs,1H), 7.94 (d,1H), 7.21-7.15 (m,3H), 6.99 (t,1H), 5.23 (bs,1H),2.63 (s,6H), 2.27 (s,3H).

Step B

Preparation of 5-Chloro2,4-dihydro-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-one

To a solution of 11.1 g 2,2-dimethyl-N-(2-methylphenyl) hydrazinecarboxamide dissolved in 600 mL methylene chloride under N₂ was added17.1 g triphosgene. The solution was heated at reflux overnight, cooled,then concentrated under reduced pressure. The resulting residue wasdissolved in ethyl acetate and washed with water, then saturated aqueousNaCl. The organic phase was dried (MgSO₄), filtered, and concentratedunder reduced pressure. The residue was purified by flash chromatography(30-50% ethyl acetate/hexanes as eluent) to afford 8.25 g (64%) of thetitle compound of Step B. ¹ H NMR (CDCl₃) δ 7.42-7.30 (m,3H), 7.17(d,1H), 3.54 (s,3H), 2.22 (s,3H).

Step C

Preparation of2,4-Dihydro-5-methoxy-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-one

8.25 g5-chloro-2,4-dihydro-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-onewas dissolved in 80 mL 1:1 dimethoxyethane/methanol under N₂. 14.0 mLsodium methoxide (30% solution in methanol) was added and the solutionwas heated at reflux for 3 h. The mixture was allowed to cool, dilutedwith ethyl acetate, washed with water, then saturated aqueous NaCl. Thecombined organic extracts were dried (MgSO₄), filtered, and concentratedunder reduced pressure. The residue was purified by flash chromatography(50-70% ethyl acetate/hexanes as eluent) and triturated with 50%diethylether/hexanes to afford 6.7 g of the title compound of Step C(95% pure). ¹ H NMR (CDCl₃) δ 7.35-7.27 (m,3H), 7.18 (d,1H), 3.94(s,3H), 3.46 (s,3H), 2.22 (s,3H).

Step D

Preparation of4-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

To a solution/suspension of 6.7 g2,4-dihydro-5-methoxy-2-methyl-4-(2-methylphenyl)-3H-1,2,4-triazol-3-onedissolved in 95 mL carbon tetrachloride under N₂ was addedN-bromosuccinimide (6.53 g) followed by a catalytic amount of benzoylperoxide. The solution was heated at reflux for 2 h. Another 1.63 gN-bromosuccinimide and a catalytic amount of benzoyl peroxide were addedand the solution was heated at reflux for an hour. After cooling,methylene chloride was added and the organic layer was washedsuccessively with water, the 0.1 N sodium thiosulfate solution, thensaturated aqueous NaCl. The combined organic extracts were dried(MgSO₄), filtered, and concentrated under reduced pressure. The residuewas purified by flash chromatography (3-10% diethylether/methylenechloride as eluent) to afford 3.12 g of the title compound of Step D. ¹H NMR (CDCl₃) δ 7.5 (m,1H), 7.44 (m,2H), 7.22 (m,1H), 4.60 (d,1H), 4.36(d,1H), 3.96 (s,3H), 3.47 (s,3H).

Step E

Preparation of2,4-Dihydro-5-methoxy-2-methyl-4-[2-[[[(phenylmethylene)-amineloxy]methyl]phenyl]-3H-1,24-triazol-3-one

0.40 g4-[2-(bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-onewas dissolved in approximately 5 mL N,N-dimethylformamide under N₂ andto this was added 0.20 g acetophenone oxime, followed by 0.07 g of 60%sodium hydride. The solution was allowed to stir 4 h at room temperaturethen was diluted with ethyl acetate, washed with water, then saturatedaqueous NaCl. The organic phase was dried (MgSO₄), filtered, andconcentrated under reduced pressure. The residue was purified by flashchromatography (60% ethyl acetate/hexanes as eluent) to afford 0.38 g ofthe title compound of Step E. ¹ H NMR (CDCl₃) δ 7.6 (m,3H), 7.44 (m2H),7.35 (m,3H), 7.25 (m,1H), 5.26 (d,1H), 5.22 (d,1H), 3.88 (s,3H), 3.40(s,3H), 2.20 (s,3H).

By the general procedures described herein, or through obviousmodifications thereof, the compound of the Tables 1-26 can be prepared.

The following abbreviations are used in the Tables which follow. Allalkyl groups are the normal isomers unless indicated otherwise.

    ______________________________________                                        n = normal   MeO = methoxy MeS = methylthio                                   i = iso      Pr = propyl   Bu = butyl                                         Me = methyl  CN = cyano    Ph = phenyl                                        Et = ethyl   c = cyclo     NO.sub.2 = nitro                                   ______________________________________                                         ##STR37##                                                                        I                                                                     

                                      TABLE 1                                     __________________________________________________________________________    Compounds of Formula I wherein: G ═ C, W ═ O, R.sup.3  ═          R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(CH.sub.3),                        Z ═ 3-CF.sub.3 -- the floating double bood is attached to to G, and       X       A  X       A  X       A  X       A                                    __________________________________________________________________________    R.sup.2  ═ Me                                                             MeO     O  MeS     O  MeO     S  MeS                                          EtO     O  EtS     O  EtO     S  EtS                                          n-PrO   O  n-PrS   O  n-PrO   S  n-PrS                                        H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                   HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                           CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                   (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                  R.sup.2  ═ Et                                                             MeO     O  MeS     O  MeO     S  MeS                                          EtO     O  EtS     O  EtO     S  EtS                                          n-PrO   O  n-PrS   O  n-PrO   S  n-PrS                                        H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                   HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                           CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                   (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                  R.sup.2  ═ Pr                                                             MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PtS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                                                           S                                    R.sup.2  ═ H                                                              MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                                                           S                                    R.sup.2  ═ Me                                                             MeO     NH MeS     NH MeO     NMe                                                                              MeS     NMe                                  EtO     NH EtS     NH EtO     NMe                                                                              Ets     NMe                                  n-PrO   NH n-PrS   NH n-PrO   NMe                                                                              n-PrS   NMe                                  H.sub.2 C═CHCH.sub.2 O                                                            NH H.sub.2 C═CHCH.sub.2 S                                                            NH H.sub.2 C═CHCH.sub.2 O                                                            NMC                                                                              H.sub.2 C═CHCH.sub.2 S                                                            NMe                                  HC.tbd.CCH.sub.2 O                                                                    NH HC.tbd.CCH.sub.2 S                                                                    NH HC.tbd.CCH.sub.2 O                                                                    NMe                                                                              HC.tbd.CCH.sub.2 S                                                                    NMe                                  CF.sub.3 O                                                                            NH CF.sub.3 S                                                                            NH CF.sub.3 O                                                                            NMe                                                                              CF.sub.3 S                                                                            NMe                                  (c-propyl)O                                                                           NH (c-propyl)S                                                                           NH (c-propyl)O                                                                           NMe                                                                              (c-propyl)S                                                                           NMe                                  R.sup.2  ═ H                                                              MeO     NH MeS     NH MeO     NMe                                                                              MeS     NMe                                  EtO     NH EtS     NH EtO     NMe                                                                              EtS     NMe                                  n-PrO   NH n-PrS   NH n-PrO   NMe                                                                              n-PrS   NMe                                  H.sub.2 C═CHCH.sub.2 O                                                            NH H.sub.2 C═CHCH.sub.2 S                                                            NH H.sub.2 C═CHCH.sub.2 O                                                            NMe                                                                              H.sub.2 C═CHCH.sub.2 S                                                            NMe                                  HC.tbd.CCH.sub.2 O                                                                    NH HC.tbd.CCH.sub.2 S                                                                    NH HC.tbd.CCH.sub.2 O                                                                    NMe                                                                              HC.tbd.CCH.sub.2 S                                                                    NMe                                  CF.sub.3 O                                                                            NH CF.sub.3 S                                                                            NH CF.sub.3 O                                                                            NMe                                                                              CF.sub.3 S                                   (c-propyl)O                                                                           NH (c-propyl)S                                                                           NH (c-propyl)O                                                                           NMe                                                                              (c-propyl)S                                  __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Compounds of Formula I wherein: G ═ N, W ═ O, R.sup.3  ═          R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(CH.sub.3), Z ═ 3-CF           the floating double bond is attached to A, and                                X       A  X       A  X       A  X       A                                    __________________________________________________________________________    R.sup.2  ═ Me                                                             MeO     N  MeS     N  MeO     CH MeO                                          EtO     N  EtS     N  EtO     CH EtO                                          n-PrO   N  n-PrS   N  n-PrO   CH n-PrO                                        H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                   HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                           CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                   (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                  R.sup.2  ═ Et                                                             MeO     N  MeS     N  MeO     CH MeO                                          EtO     N  EtS     N  EtO     CH EtO                                          n-PrO   N  n-PrS   N  n-PrO   CH n-PrO                                        H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                   HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                           CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                   (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                  R.sup.2  ═ n-Pr                                                           MeO     N  MeS     N  MeO     CH MeO                                          EtO     N  EtS     N  EtO     CH EtO                                          n-PrO   N  n-PrS   N  n-PrO   CH n-PrO                                        H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                   HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                           CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                   (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                  R.sup.2  ═ H                                                              MeO     N  MeS     N  MeO     CH MeO     CH                                   EtO     N  EtS     N  EtO     CH EtO     CH                                   n-PrO   N  n-PrS   N  n-PrO   CH n-PrO   CH                                   H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                                                            CH                                   HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                                                                    CH                                   CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                                                            CH                                   (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                                                           CH                                   R.sup.2  ═ Me                                                             MeO     CMe                                                                              MeS     CMe                                                                              MeO     CEt                                                                              MeO     CEt                                  EtO     CMe                                                                              EtS     CMe                                                                              EtO     CEt                                                                              EtO     CEt                                  n-PrO   CMe                                                                              n-PrS   CMe                                                                              n-PrO   CEt                                                                              n-PrO   CEt                                  H.sub.2 C═CHCH.sub.2 O                                                            CMe                                                                              H.sub.2 C═CHCH.sub.2 S                                                            CMe                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CEt                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CEt                                  HC.tbd.CCH.sub.2 O                                                                    CMe                                                                              HC.tbd.CCH.sub.2 S                                                                    CMe                                                                              HC.tbd.CCH.sub.2 O                                                                    CEt                                                                              HC.tbd.CCH.sub.2 O                                                                    CEt                                  CF.sub.3 O                                                                            CMe                                                                              CF.sub.3 S                                                                            CMe                                                                              CF.sub.3 O                                                                            CEt                                                                              CF.sub.3 O                                                                            CEt                                  (c-propyl)O                                                                           CMe                                                                              (c-propyl)S                                                                           CMe                                                                              (c-propyl)O                                                                           CEt                                                                              (c-propyl)O                                                                           CEt                                  R.sup.2  ═ H                                                              MeO     CEt                                                                              MeS     CEt                                                                              MeO     CMe                                                                              MeO     CMe                                  EtO     CEt                                                                              EtS     CEt                                                                              EtO     CMe                                                                              EtO     CMe                                  n-PrO   CEt                                                                              n-PrS   CEt                                                                              n-PrO   CMe                                                                              n-PrO   CMe                                  H.sub.2 C═CHCH.sub.2 O                                                            CEt                                                                              H.sub.2 C═CHCH.sub.2 S                                                            CEt                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CMe                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CMe                                  HC.tbd.CCH.sub.2 O                                                                    CEt                                                                              HC.tbd.CCH.sub.2 S                                                                    CEt                                                                              HC.tbd.CCH.sub.2 O                                                                    CMe                                                                              HC.tbd.CCH.sub.2 O                                                                    CMe                                  CF.sub.3 O                                                                            CEt                                                                              CF.sub.3 S                                                                            CEt                                                                              CF.sub.3 O                                                                            CMe                                                                              CF.sub.3 O                                                                            CMe                                  (c-propyl)O                                                                           CEt                                                                              (c-propyl)S                                                                           CEt                                                                              (c-propyl)O                                                                           CMe                                                                              (c-propyl)O                                                                           CMe                                  __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________    Compounds of Formula I wherein: G ═ C, W ═ O, R.sup.3  ═          R.sup.4  ═ H, Y ═ CH.sub.2 O, Z ═ 2-Me--Ph,                       the floating double bond is attached to G, and                                X       A  X       A  X       A  X       A                                    __________________________________________________________________________    R.sup.2  ═ Me                                                             MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                                                           S                                    R.sup.2  ═ Et                                                             MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                                                           S                                    R.sup.2  ═ n-Pr                                                           MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                                                           S                                    R.sup.2  ═ H                                                              MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    (c-propyl)O                                                                           O  (c-propyl)S                                                                           O  (c-propyl)O                                                                           S  (c-propyl)S                                                                           S                                    R.sup.2  ═ Me                                                             MeO     NH MeS     NH MeO     NMe                                                                              MeS     NMe                                  EtO     NH EtS     NH EtO     NMe                                                                              EtS     NMe                                  n-PrO   NH n-PrS   NH n-PrO   NMe                                                                              n-PrS   NMe                                  H.sub.2 C═CHCH.sub.2 O                                                            NH H.sub.2 C═CHCH.sub.2 S                                                            NH H.sub.2 C═CHCH.sub.2 O                                                            NMe                                                                              H.sub.2 C═CHCH.sub.2 S                                                            NMe                                  HC.tbd.CCH.sub.2 O                                                                    NH HC.tbd.CCH.sub.2 S                                                                    NH HC.tbd.CCH.sub.2 O                                                                    NMe                                                                              HC.tbd.CCH.sub.2 S                                                                    NMe                                  CF.sub.3 O                                                                            NH CF.sub.3 S                                                                            NH CF.sub.3 O                                                                            NMe                                                                              CF.sub.3 S                                                                            NMe                                  (c-propyl)O                                                                           NH (c-propyl)S                                                                           NH (c-propyl)O                                                                           NMe                                                                              (c-propyl)S                                                                           NMe                                  R.sup.2  ═ H                                                              MeO     NH MeS     NH MeO     NMe                                                                              MeS     NMe                                  EtO     NH EtS     NH EtO     NMe                                                                              EtS     NMe                                  n-PrO   NH n-PrS   NH n-PrO   NMe                                                                              n-PrS   NMe                                  H.sub.2 C═CHCH.sub.2 O                                                            NH H.sub.2 C═CHCH.sub.2 S                                                            NH H.sub.2 C═CHCH.sub.2 O                                                            NMe                                                                              H.sub.2 C═CHCH.sub.2 S                                                            NMe                                  HC.tbd.CCH.sub.2 O                                                                    NH HC.tbd.CCH.sub.2 S                                                                    NH HC.tbd.CCH.sub.2 O                                                                    NMe                                                                              HC.tbd.CCH.sub.2 S                                                                    NMe                                  CF.sub.3 O                                                                            NH CF.sub.3 S                                                                            NH CF.sub.3 O                                                                            NMe                                                                              CF.sub.3 S                                                                            NMe                                  (c-propyl)O                                                                           NH (c-propyl)S                                                                           NH (c-propyl)O                                                                           NMe                                                                              (c-propyl)S                                                                           NMe                                  __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________    Compounds of Formula I wherein: G ═ N, W ═ O, R.sup.3  ═          R.sup.4  ═ H, Y ═ CH.sub.2 O, Z ═ 2-Me--Ph,                       the floating double bond is attached to A, and                                X       A  X       A  X       A  X       A                                    __________________________________________________________________________    R.sup.2  ═ Me                                                             MeO     N  MeS     N  MeO     CH MeO     CH                                   EtO     N  EtS     N  EtO     CH EtO     CH                                   n-PrO   N  n-PrS   N  n-PrO   CH n-PrO   CH                                   H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                                                            CH                                   HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                                                                    CH                                   CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                                                            CH                                   (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                                                           CH                                   R.sup.2  ═ Et                                                             MeO     N  MeS     N  MeO     CH MeO     CH                                   EtO     N  EtS     N  EtO     CH EtO     CH                                   n-PrO   N  n-PrS   N  n-PrO   CH n-PrO   C                                    H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                                                            C                                    HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                                                                    C                                    CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                                                            C                                    (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                                                           C                                    R.sup.2  ═ n-Pr                                                           MeO     N  MeS     N  MeO     CH MeO     C                                    EtO     N  EtS     N  EtO     CH EtO     C                                    n-PrO   N  n-PrS   N  n-PrO   CH n-PrO   C                                    H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                                                            C                                    HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                                                                    C                                    CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                                                            C                                    (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                                                           C                                    R.sup.2  ═ H                                                              MeO     N  MeS     N  MeO     CH MeO     C                                    EtO     N  EtS     N  EtO     CH EtO     C                                    n-PrO   N  n-PrS   N  n-PrO   CH n-PrO   C                                    H.sub.2 C═CHCH.sub.2 O                                                            N  H.sub.2 C═CHCH.sub.2 S                                                            N  H.sub.2 C═CHCH.sub.2 O                                                            CH H.sub.2 C═CHCH.sub.2 O                                                            C                                    HC.tbd.CCH.sub.2 O                                                                    N  HC.tbd.CCH.sub.2 S                                                                    N  HC.tbd.CCH.sub.2 O                                                                    CH HC.tbd.CCH.sub.2 O                                                                    C                                    CF.sub.3 O                                                                            N  CF.sub.3 S                                                                            N  CF.sub.3 O                                                                            CH CF.sub.3 O                                                                            C                                    (c-propyl)O                                                                           N  (c-propyl)S                                                                           N  (c-propyl)O                                                                           CH (c-propyl)O                                                                           C                                    R.sup.2  ═ Me                                                             MeO     CMe                                                                              MeS     CMe                                                                              MeO     CEt                                                                              MeO     C                                    EtO     CMe                                                                              EtS     CMe                                                                              EtO     CEt                                                                              EtO     C                                    n-PrO   CMe                                                                              n-PrS   CMe                                                                              n-PrO   CEt                                                                              n-PrO   C                                    H.sub.2 C═CHCH.sub.2 O                                                            CMe                                                                              H.sub.2 C═CHCH.sub.2 S                                                            CMe                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CEt                                                                              H.sub.2 C═CHCH.sub.2 O                                                            C                                    HC.tbd.CCH.sub.2 O                                                                    CMe                                                                              HC.tbd.CCH.sub.2 S                                                                    CMe                                                                              HC.tbd.CCH.sub.2 O                                                                    CEt                                                                              HC.tbd.CCH.sub.2 O                                                                    C                                    CF.sub.3 O                                                                            CMe                                                                              CF.sub.3 S                                                                            CMe                                                                              CF.sub.3 O                                                                            CEt                                                                              CF.sub.3 O                                                                            C                                    (c-propyl)O                                                                           CMe                                                                              (c-propyl)S                                                                           CMe                                                                              (c-propyl)O                                                                           CEt                                                                              (c-propyl)O                                                                           C                                    R.sup.2  ═ H                                                              MeO     CEt                                                                              MeS     CEt                                                                              MeO     CMe                                                                              MeO     CMe                                  EtO     CEt                                                                              EtS     CEt                                                                              EtO     CMe                                                                              EtO     CMe                                  n-PrO   CEt                                                                              n-PrS   CEt                                                                              n-PrO   CMe                                                                              n-PrO   CMe                                  H.sub.2 C═CHCH.sub.2 O                                                            CEt                                                                              H.sub.2 C═CHCH.sub.2 S                                                            CEt                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CMe                                                                              H.sub.2 C═CHCH.sub.2 O                                                            CMe                                  HC.tbd.CCH.sub.2 O                                                                    CEt                                                                              HC.tbd.CCH.sub.2 S                                                                    CEt                                                                              HC.tbd.CCH.sub.2 O                                                                    CMe                                                                              HC.tbd.CCH.sub.2 O                                                                    CMe                                  CF.sub.3 O                                                                            CEt                                                                              CF.sub.3 S                                                                            CEt                                                                              CF.sub.3 O                                                                            CMe                                                                              CF.sub.3 O                                                                            CMe                                  (c-propyl)O                                                                           CEt                                                                              (c-propyl)S                                                                           CEt                                                                              (c-propyl)O                                                                           CMe                                                                              (c-propyl)O                                                                           CMe                                  __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________    Compounds of Formula I wherein: G ═ C, W ═ S, R.sup.3  ═          R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(CH.sub.3),                        Z ═ 3-CF.sub.3 -Ph, the floating double bond is attached to G, and        R.sup.2  ═ Me                                                             X       A  X       A  X       A  X       A                                    __________________________________________________________________________    MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  EtS     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    MeO     NH MeO     NMe                                                                              MeO     NEt                                                                              MeS     NPr                                  __________________________________________________________________________

                  TABLE 6                                                         ______________________________________                                        Compounds of Formula I wherein: A ═ N, G ═ N, W ═ S,              R.sup.3  ═ R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(Me), Z ═       3-CF.sub.3 --Ph,                                                              the floating double bond is attached to A, and                                R.sup.2  ═ Me                                                             X            X          X        X                                            ______________________________________                                        MeO          EtO        n-PrO    H.sub.2 C═CHCH.sub.2 O                   HC.tbd.CCH.sub.2 O                                                                         CF.sub.3 O OCF.sub.2 H                                                                            OCH.sub.2 CF.sub.3                           (c-propyl)O  MeS        EtS      n-PrS                                        H.sub.2 C═CHCH.sub.2 S                                                                 HC.tbd.CCH.sub.2 S                                                                       CF.sub.3 S                                                                             (c-propyl)S                                  ______________________________________                                    

                                      TABLE 7                                     __________________________________________________________________________    Compounds of Formula I wherein: G ═ C, W ═ S, R.sup.3  ═          R.sup.4  ═ H, Y ═ CH.sub.2 O, Z ═ 2-Me--Ph,                       the floating double bond is attached to G, and                                R.sup.2  ═ Me                                                             X       A  X       A  X       A  X       A                                    __________________________________________________________________________    MeO     O  MeS     O  MeO     S  MeS     S                                    EtO     O  EtS     O  EtO     S  Ets     S                                    n-PrO   O  n-PrS   O  n-PrO   S  n-PrS   S                                    H.sub.2 C═CHCH.sub.2 O                                                            O  H.sub.2 C═CHCH.sub.2 S                                                            O  H.sub.2 C═CHCH.sub.2 O                                                            S  H.sub.2 C═CHCH.sub.2 S                                                            S                                    HC.tbd.CCH.sub.2 O                                                                    O  HC.tbd.CCH.sub.2 S                                                                    O  HC.tbd.CCH.sub.2 O                                                                    S  HC.tbd.CCH.sub.2 S                                                                    S                                    CF.sub.3 O                                                                            O  CF.sub.3 S                                                                            O  CF.sub.3 O                                                                            S  CF.sub.3 S                                                                            S                                    MeO     NH MeO     NMe                                                                              MeO     NEt                                                                              MeS     N                                    __________________________________________________________________________

                  TABLE 8                                                         ______________________________________                                        Compounds of Formula I wherein: A ═ N, G ═ N, W ═ S,              R.sup.3  ═ R.sup.4  ═ H, Y ═ CH.sub.2 O, Z ═ 2-Me--Ph,        floating double bond is attached to A, and                                    R.sup.2  ═ Me                                                             X            X          X        X                                            ______________________________________                                        MeO          EtO        n-PrO    H.sub.2 C═CHCH.sub.2 O                   HC.tbd.CCH.sub.2 O                                                                         CF.sub.3 O OCF.sub.2 H                                                                            OCH.sub.2 CF.sub.3                           (c-propyl)O  MeS        EtS      n-PrS                                        H.sub.2 C═CHCH.sub.2 S                                                                 HC.tbd.CCH.sub.2 S                                                                       CF.sub.3 S                                                                             (c-propyl)S                                  ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Compounds of Formula I wherein: G ═ C, A ═ W ═ O, X ═         MeO,                                                                          R.sup.2  ═ Me, Y ═ CH.sub.2 ON═C(Me), Z ═ 3-CF.sub.3          --Ph,                                                                         the following floating double bond is attached to G, and                      R.sup.3  R.sup.4                                                                              R.sup.3    R.sup.4                                                                            R.sup.3                                                                              R.sup.4                                ______________________________________                                        3-F      H      5-NO.sub.2 H    3-F    5-F                                    5-F      H      6-Me       H    3-Cl   5-Cl                                   3-Cl     H      3-Me       H    4-Me   5-Cl                                   4-Cl     H      4-MeO      H    3-F    5-CF.sub.3                             5-Br     H      5-CF.sub.3 O                                                                             H    3-Cl   5-NO.sub.2                             4-CF.sub.3                                                                             H      5-allyl    H    6-CF.sub.3 O                                                                         H                                      5-CN     H      4-propargyl                                                                              H    5-Pr   H                                      ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        Compounds of Formula I wherein: A ═ N, G ═ N, W ═ O, X ═      MeO,                                                                          R.sup.2  ═ Me, Y ═ CH.sub.2 ON═C(Me), Z ═ 3-CF.sub.3          -Ph,                                                                          the floating double bond is attached to A, and                                R.sup.3  R.sup.4                                                                              R.sup.3    R.sup.4                                                                            R.sup.3                                                                              R.sup.4                                ______________________________________                                        3-F      H      5-NO.sub.2 H    3-F    5-F                                    5-F      H      6-Me       H    3-Cl   5-Cl                                   3-Cl     H      3-Me       H    4-Me   5-Cl                                   4-Cl     H      4-MeO      H    3-F    5-CF.sub.3                             5-Br     H      5-CF.sub.3 O                                                                             H    3-Cl   5-NO.sub.2                             4-CF.sub.3                                                                             H      5-allyl    H    6-CF.sub.3 O                                                                         H                                      5-CN     H      4-propargyl                                                                              H    5-Pr   H                                      ______________________________________                                    

                                      TABLE 11                                    __________________________________________________________________________    Compounds of Formula I wherein: A = O, G = C, W = O, X = MeO, R.sup.2 =       Me, the floating                                                              double bond is attached to G, and                                              ##STR38##                                                                    is                                                                            __________________________________________________________________________     ##STR39##                                                                               ##STR40##                                                                                  ##STR41##                                                                                  ##STR42##                                __________________________________________________________________________

                                      TABLE 12                                    __________________________________________________________________________    Compounds of Formula I wherein: A = N, G = N, W = O, X = MeO, R.sup.2 =       Me, the floating                                                              double bond is attached to A, and                                              ##STR43##                                                                    is                                                                            __________________________________________________________________________     ##STR44##                                                                               ##STR45##                                                                                  ##STR46##                                                                                  ##STR47##                                __________________________________________________________________________

                                      TABLE 13                                    __________________________________________________________________________    Compounds of Formula I wherein: G ═ C, W ═ O, X ═ MeO,            R.sup.2  ═ Me,                                                            R.sup.3  ═ R.sup.4  ═ H, Z ═ Ph,                                  the floating double bond is attached to G, and                                Y      Y       Y    Y        Y                                                __________________________________________________________________________    A ═ O                                                                     S      CH.sub.2 CH.sub.2                                                                     CH(Me)O                                                                            SCH.sub.2                                                                              C(Me)═N--O                                   CH═CH                                                                            CH(Me)CH.sub.2                                                                        OCH.sub.2                                                                          SCH(Me)  O--N═CH                                      C(Me)═CH                                                                         CH.sub.2 CH(Me)                                                                       OCH(Me)                                                                            CH.sub.2 O--N═CH                                                                   O--N═C(Me)                                   CH═C(Me)                                                                         CH(Me)CH(Me)                                                                          CH.sub.2 S                                                                         CH.sub.2 O--N═C(Me)                                                                CH.sub.2 OC(═O)                              C(Me)═C(Me)                                                                      CH.sub.2 O                                                                            CH(Me)S                                                                            CH═N--O                                                                            CH(Me)OC(═O)                                 direct bond                                                                          C.tbd.C                                                                A ═ S                                                                     S      CH.sub.2 CH.sub.2                                                                     CH(Me)O                                                                            SCH.sub.2                                                                              C(Me)═N--O                                   CH═CH                                                                            CH(Me)CH.sub.2                                                                        OCH.sub.2                                                                          SCH(Me)  O--N═CH                                      C(Me)═CH                                                                         CH.sub.2 CH(Me)                                                                       OCH(Me)                                                                            CH.sub.2 O--N═CH                                                                   O--N═C(Me)                                   CH═C(Me)                                                                         CH(Me)CH(Me)                                                                          CH.sub.2 S                                                                         CH.sub.2 O--N═C(Me)                                                                CH.sub.2 OC(═O)                              C(Me)═C(Me)                                                                      CH.sub.2 O                                                                            CH(Me)S                                                                            CH═N--O                                                                            CH(Me)OC(═O)                                 direct bond                                                                          C.tbd.C                                                                A ═ NMe                                                                   S      CH.sub.2 CH.sub.2                                                                     CH(Me)O                                                                            SCH.sub.2                                                                              C(Me)═N--O                                   CH═CH                                                                            CH(Me)CH.sub.2                                                                        OCH.sub.2                                                                          SCH(Me)  O--N═CH                                      C(Me)═CH                                                                         CH.sub.2 CH(Me)                                                                       OCH(Me)                                                                            CH.sub.2 O--N═CH                                                                   O--N═C(Me)                                   CH═C(Me)                                                                         CH(Me)CH(Me)                                                                          CH.sub.2 S                                                                         CH.sub.2 O--N═C(Me)                                                                CH.sub.2 OC(═O)                              C(Me)═C(Me)                                                                      CH.sub.2 O                                                                            CH(Me)S                                                                            CH═N--O                                                                            CH(Me)OC(═O)                                 direct bond                                                                          C.tbd.C                                                                __________________________________________________________________________

                                      TABLE 14                                    __________________________________________________________________________    Compounds of Formula I wherein: G ═ N, W ═ O, X ═ MeO,            R.sup.2  ═ Me,                                                            R.sup.3  ═ R.sup.4  ═ H, Z ═ Ph,                                  the floating double bond is attached to A, and                                Y      Y       Y    Y        Y                                                __________________________________________________________________________    A ═ N                                                                     S      CH.sub.2 CH.sub.2                                                                     CH(Me)O                                                                            SCH.sub.2                                                                              C(Me)═N--O                                   CH═CH                                                                            CH(Me)CH.sub.2                                                                        OCH.sub.2                                                                          SCH(Me)  O--N═CH                                      C(Me)═CH                                                                         CH.sub.2 CH(Me)                                                                       OCH(Me)                                                                            CH.sub.2 O--N═CH                                                                   O--N═C(Me)                                   CH═C(Me)                                                                         CH(Me)CH(Me)                                                                          CH.sub.2 S                                                                         CH.sub.2 O--N═C(Me)                                                                CH.sub.2 OC(═O)                              C(Me)═C(Me)                                                                      CH.sub.2 O                                                                            CH(Me)S                                                                            CH═N--O                                                                            CH(Me)OC(═O)                                 direct bond                                                                          C.tbd.C                                                                A ═ S                                                                     S      CH.sub.2 CH.sub.2                                                                     CH(Me)O                                                                            SCH.sub.2                                                                              C(Me)═N--O                                   CH═CH                                                                            CH(Me)CH.sub.2                                                                        OCH.sub.2                                                                          SCH(Me)  O--N═CH                                      C(Me)═CH                                                                         CH.sub.2 CH(Me)                                                                       OCH(Me)                                                                            CH.sub.2 O--N═CH                                                                   O--N═C(Me)                                   CH═C(Me)                                                                         CH(Me)CH(Me)                                                                          CH.sub.2 S                                                                         CH.sub.2 O--N═C(Me)                                                                CH.sub.2 OC(═O)                              C(Me)═C(Me)                                                                      CH.sub.2 O                                                                            CH(Me)S                                                                            CH═N--O                                                                            CH(Me)OC(═O)                                 direct bond                                                                          C.tbd.C                                                                A ═ NMe                                                                   S      CH.sub.2 CH.sub.2                                                                     CH(Me)O                                                                            SCH.sub.2                                                                              C(Me)═N--O                                   CH═CH                                                                            CH(Me)CH.sub.2                                                                        OCH.sub.2                                                                          SCH(Me)  O--N═CH                                      C(Me)═CH                                                                         CH.sub.2 CH(Me)                                                                       OCH(Me)                                                                            CH.sub.2 O--N═CH                                                                   O--N═C(Me)                                   CH═C(Me)                                                                         CH(Me)CH(Me)                                                                          CH.sub.2 S                                                                         CH.sub.2 O--N═C(Me)                                                                CH.sub.2 OC(═O)                              C(Me)═C(Me)                                                                      CH.sub.2 O                                                                            CH(Me)S                                                                            CH═N--O                                                                            CH(Me)OC(═O)                                 direct bond                                                                          C.tbd.C                                                                __________________________________________________________________________

                                      TABLE 15                                    __________________________________________________________________________    Compounds of Formula I wherein: G ═ C, W ═ O, X ═ MeO,            R.sup.2  ═ Me, R.sup.3  ═ R.sup.4  ═ H,                           the floating double bond is attached to G, and                                Z       Z        Z         Z                                                  __________________________________________________________________________    Y ═ O, A ═ O                                                          hexyl   4-octenyl                                                                              3-pentynyl                                                                              4-PhO-2-pyridinyl                                  PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                    PhC.tbd.CCH.sub.2                                                                       (c-propyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph 2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                        2-CN--Ph                                                                              2-F--Ph  2-Cl--Ph  6-PhO-4-pyrimidinyl                                2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                          2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                                2-CF.sub.3 --Ph                                                                       4-Ph--Ph 3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                            2-I--Ph 3-(2-Cl--PhO)--Ph                                                                      3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                    c-hexyl 3,5-diCl--Ph                                                                           6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                               4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                    6-PhO-4-pyridinyl                                                                       3-pyridinyl                                        PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph                                                                              3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyrindinyloxy-Ph                         (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                          3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                    CF.sub.3 CH.sub.2                                                                     3-(2-CN-PhO(--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                                2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                      5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                 i-Bu    6-Me-2-pyridinyl                                                                       6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                        2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                       6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)-4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph 6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                            4-Cl--Ph                                                                              3-Et--Ph 2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                             3-Me--Ph                                                                              4-Et--Ph 4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                          3-CF.sub.3 --Ph                                                                       4-MeO--Ph                                                                              4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                            3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                             4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                          3-t-Bu--Ph                                                                            4-CN--Ph 6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                        3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                        2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                            3-F--Ph 4-F--Ph  3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                            4-CF.sub.3 --Ph                                                                       3-Ph--Ph 5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                  3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                           2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                   3,4-diCF.sub.3 --Ph                                                                   3,5-diMe--Ph                                                                           3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                   3-EtO--Ph                                                                             3-MeS-Ph 4-OCF.sub.2 H--Ph                                            Y ═ CH.sub.2 O, A ═ O                                                 hexyl   4-octenyl                                                                              3-pentynyl                                                                              4-PhO-2-pyridinyl                                  PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                    PhC.tbd.CCH.sub.2                                                                       (c-propyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph 2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                        2-CN--Ph                                                                              2-F--Ph  2-Cl--Ph  6-PhO-4-pyrimidinyl                                2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                          2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                                2-CF.sub.3 --Ph                                                                       4-Ph--Ph 3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                            2-I--Ph 3-(2-Cl--PhO)--Ph                                                                      3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                    c-hexyl 3,5-diCl--Ph                                                                           6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                               4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                    6-PhO-4-pyridinyl                                                                       3-pyridinyl                                        PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph                                                                              3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyrindinyloxy-Ph                         (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                          3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                    CF.sub.3 CH.sub.2                                                                     3-(2-CN-PhO(--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                                2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                      5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                 i-Bu    6-Me-2-pyridinyl                                                                       6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                        2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                       6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)-4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph 6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                            4-Cl--Ph                                                                              3-Et--Ph 2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                             3-Me--Ph                                                                              4-Et--Ph 4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                          3-CF.sub.3 --Ph                                                                       4-MeO--Ph                                                                              4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                            3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                             4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                          3-t-Bu--Ph                                                                            4-CN--Ph 6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                        3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                        2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                            3-F--Ph 4-F--Ph  3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                            4-CF.sub.3 --Ph                                                                       3-Ph--Ph 5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                  3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                           2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                   3,4-diCF.sub.3 --Ph                                                                   3,5-diMe--Ph                                                                           3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                   3-EtO--Ph                                                                             3-MeS-Ph 4-OCF.sub.2 H--Ph                                            Y ═ O, A ═ NMe                                                        hexyl   4-octenyl                                                                              3-pentynyl                                                                              4-PhO-2-pyridinyl                                  PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                    PhC.tbd.CCH.sub.2                                                                       (c-propyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph 2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                        2-CN--Ph                                                                              2-F--Ph  2-Cl--Ph  6-PhO-4-pyrimidinyl                                2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                          2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                                2-CF.sub.3 --Ph                                                                       4-Ph--Ph 3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                            2-I--Ph 3-(2-Cl--PhO)--Ph                                                                      3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                    c-hexyl 3,5-diCl--Ph                                                                           6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                               4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                    6-PhO-4-pyridinyl                                                                       3-pyridinyl                                        PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph                                                                              3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyrindinyloxy-Ph                         (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                          3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                    CF.sub.3 CH.sub.2                                                                     3-(2-CN-PhO(--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                                2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                      5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                 i-Bu    6-Me-2-pyridinyl                                                                       6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                        2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                       6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)-4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph 6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                            4-Cl--Ph                                                                              3-Et--Ph 2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                             3-Me--Ph                                                                              4-Et--Ph 4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                          3-CF.sub.3 --Ph                                                                       4-MeO--Ph                                                                              4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                            3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                             4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                          3-t-Bu--Ph                                                                            4-CN--Ph 6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                        3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                        2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                            3-F--Ph 4-F--Ph  3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                            4-CF.sub.3 --Ph                                                                       3-Ph--Ph 5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                  3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                           2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                   3,4-diCF.sub.3 --Ph                                                                   3,5-diMe--Ph                                                                           3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                   3-EtO--Ph                                                                             3-MeS-Ph 4-OCF.sub.2 H--Ph                                            Y ═ CH.sub.2 O, A ═ NMe                                               hexyl   4-octenyl                                                                              3-pentynyl                                                                              4-PhO-2-pyridinyl                                  PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                    PhC.tbd.CCH.sub.2                                                                       (c-propyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph 2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                        2-CN--Ph                                                                              2-F--Ph  2-Cl--Ph  6-PhO-4-pyrimidinyl                                2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                          2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                                2-CF.sub.3 --Ph                                                                       4-Ph--Ph 3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                            2-I--Ph 3-(2-Cl--PhO)--Ph                                                                      3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                    c-hexyl 3,5-diCl--Ph                                                                           6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                               4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                    6-PhO-4-pyridinyl                                                                       3-pyridinyl                                        PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph                                                                              3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyrindinyloxy-Ph                         (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                          3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                    CF.sub.3 CH.sub.2                                                                     3-(2-CN-PhO(--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                                2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                      5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                 i-Bu    6-Me-2-pyridinyl                                                                       6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                        2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                       6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)-4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph 6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                            4-Cl--Ph                                                                              3-Et--Ph 2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                             3-Me--Ph                                                                              4-Et--Ph 4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                          3-CF.sub.3 --Ph                                                                       4-MeO--Ph                                                                              4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                            3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                             4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                          3-t-Bu--Ph                                                                            4-CN--Ph 6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                        3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                        2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                            3-F--Ph 4-F--Ph  3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                            4-CF.sub.3 --Ph                                                                       3-Ph--Ph 5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                  3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                           2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                   3,4-diCF.sub.3 --Ph                                                                   3,5-diMe--Ph                                                                           3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                   3-EtO--Ph                                                                             3-MeS-Ph 4-OCF.sub.2 H--Ph                                            __________________________________________________________________________

                                      TABLE 16                                    __________________________________________________________________________    Compound of Formula I wherein: A ═ O, G ═ C, W ═ O, X ═       MeO, R.sup.2  ═ Me,                                                       R.sup.3  ═ R.sup.4  ═ H, the floating double bond is attached to      G, and                                                                        Y ═ CH.sub.2 ON═C(CH.sub.3).                                          Z       Z         Z         Z                                                 __________________________________________________________________________    hexyl   4-octenyl 3-pentynyl                                                                              4-PhO-2-pyridinyl                                 PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                     PhC.tbd.CCH.sub.2                                                                       (cpropyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph  2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                       2-CN--Ph                                                                              2-F--Ph   2-Cl--Ph  6-PhO-4-pyrimidinyl                               2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                           2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                               2-CF.sub.3 --Ph                                                                       4-Ph--Ph  3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                           2-I--Ph 3-(2-Cl--PhO)--Ph                                                                       3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                   c-hexyl 3,5-diCl--Ph                                                                            6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                              4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                     6-PhO-4-pyridinyl                                                                       3-pyridinyl                                       PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph 3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyridinyloxy)-Ph                        (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                           3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                   CF.sub.3 CH.sub.2                                                                     3-(2-CN--PhO)--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                               2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                       5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                i-Bu    6-Me-2-pyridinyl                                                                        6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                       2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                        6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph  6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                           4-Cl--Ph                                                                              3-Et--Ph  2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                            3-Me--Ph                                                                              4-Et--Ph  4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                         3-CF.sub.3 --Ph                                                                       4-MeO--Ph 4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                           3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                              4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                         3-t-Bu--Ph                                                                            4-CN--Ph  6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                       3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                         2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                           3-F--Ph 4-F--Ph   3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                           4-CF.sub.3 --Ph                                                                       3-Ph--Ph  5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                 3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                            2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                  3,4-diCF.sub.3 --Ph                                                                   3,5,-diMe-Ph                                                                            3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                  3-EtO--Ph                                                                             3-Mes--Ph 4-OCF.sub.2 2H--Ph                                          __________________________________________________________________________

                                      TABLE 17                                    __________________________________________________________________________    Compound of Formula I wherein: A ═ NMe, G ═ C, W ═ O, X ═     MeO, R.sup.2  ═ Me,                                                       R.sup.3  ═ R.sup.4  ═ H, the floating double bond is attached to      G, and                                                                        Y ═ CH.sub.2 ON═C(CH.sub.3).                                          Z       Z         Z         Z                                                 __________________________________________________________________________    hexyl   4-octenyl 3-pentynyl                                                                              4-PhO-2-pyridinyl                                 PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                     PhC.tbd.CCH.sub.2                                                                       (cpropyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph  2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                       2-CN--Ph                                                                              2-F--Ph   2-Cl--Ph  6-PhO-4-pyrimidinyl                               2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                           2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                               2-CF.sub.3 --Ph                                                                       4-Ph--Ph  3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                           2-I--Ph 3-(2-Cl--PhO)--Ph                                                                       3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                   c-hexyl 3,5-diCl--Ph                                                                            6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                              4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                     6-PhO-4-pyridinyl                                                                       3-pyridinyl                                       PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph 3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyridinyloxy)-Ph                        (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                           3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                   CF.sub.3 CH.sub.2                                                                     3-(2-CN--PhO)--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                               2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                       5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                i-Bu    6-Me-2-pyridinyl                                                                        6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                       2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                        6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph  6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                           4-Cl--Ph                                                                              3-Et--Ph  2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                            3-Me--Ph                                                                              4-Et--Ph  4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                         3-CF.sub.3 --Ph                                                                       4-MeO--Ph 4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                           3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                              4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                         3-t-Bu--Ph                                                                            4-CN--Ph  6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                       3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                         2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                           3-F--Ph 4-F--Ph   3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                           4-CF.sub.3 --Ph                                                                       3-Ph--Ph  5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                 3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                            2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                  3,4-diCF.sub.3 --Ph                                                                   3,5,-diMe-Ph                                                                            3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                  3-EtO--Ph                                                                             3-Mes--Ph 4-OCF.sub.2 2H--Ph                                          __________________________________________________________________________

                                      TABLE 18                                    __________________________________________________________________________    Compounds of Formula I wherein: A ═ N, G ═ N, W ═ O, X ═      MeO, R.sup.2  ═Me,                                                        R.sup.3  ═R.sup.4  ═ H, the floating double bond is attached to       A, and                                                                        Z       Z         Z         Z                                                 __________________________________________________________________________    Y ═ CH.sub.2 ON═C(CH.sub.3).                                          hexyl   4-octenyl 3-pentynyl                                                                              4-PhO-2-pyridinyl                                 PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                     PhC.tbd.CCH.sub.2                                                                       (cpropyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph  2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                       2-CN--Ph                                                                              2-F--Ph   2-Cl--Ph  6-PhO-4-pyrimidinyl                               2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                           2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                               2-CF.sub.3 --Ph                                                                       4-Ph--Ph  3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                           2-I--Ph 3-(2-Cl--PhO)--Ph                                                                       3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                   c-hexyl 3,5-diCl--Ph                                                                            6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                              4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                     6-PhO-4-pyridinyl                                                                       3-pyridinyl                                       PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph 3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyridinyloxy)-Ph                        (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                           3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                   CF.sub.3 CH.sub.2                                                                     3-(2-CN--PhO)--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                               2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                       5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                i-Bu    6-Me-2-pyridinyl                                                                        6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                       2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                        6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph  6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                           4-Cl--Ph                                                                              3-Et--Ph  2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                            3-Me--Ph                                                                              4-Et--Ph  4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                         3-CF.sub.3 --Ph                                                                       4-MeO--Ph 4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                           3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                              4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                         3-t-Bu--Ph                                                                            4-CN--Ph  6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                       3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                         2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                           3-F--Ph 4-F--Ph   3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                           4-CF.sub.3 --Ph                                                                       3-Ph--Ph  5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                 3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                            2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                  3,4-diCF.sub.3 --Ph                                                                   3,5,-diMe-Ph                                                                            3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                  3-EtO--Ph                                                                             3-Mes--Ph 4-OCF.sub.2 2H--Ph                                          Y ═ CH.sub.2 S.                                                           hexyl   4-octenyl 3-pentynyl                                                                              4-PhO-2-pyridinyl                                 PhO(CH.sub.2).sub.3                                                                   PhCH═CHCH.sub.2                                                                     PhC.tbd.CCH.sub.2                                                                       (cpropyl)CH.sub.2                                 2-Br--Ph                                                                              2-Me--Ph  2-Et--Ph  6-(2-CN--PhO)-4-pyrimidinyl                       2-CN--Ph                                                                              2-F--Ph   2-Cl--Ph  6-PhO-4-pyrimidinyl                               2,4-diCl--Ph                                                                          2-Me-4-Cl--Ph                                                                           2,4,6-triCl--Ph                                                                         4-EtO-2-pyrimidinyl                               2-CF.sub.3 --Ph                                                                       4-Ph--Ph  3-PhO--Ph 3-(4-pyrimidinyloxy)-Ph                           2-I--Ph 3-(2-Cl--PhO)--Ph                                                                       3-(2-Et--PhO)--Ph                                                                       4-(2-thienyl)Ph                                   c-hexyl 3,5-diCl--Ph                                                                            6-Ph-2-pyridinyl                                                                        3-(2-pyridinyloxy)Ph                              4-NO.sub.2 --Ph                                                                       3,5-diCF.sub.3 --Ph                                                                     6-PhO-4-pyridinyl                                                                       3-pyridinyl                                       PhCH.sub.2 CH.sub.2                                                                   2-MeO--Ph 3-thienyloxy-Ph                                                                         4-(3-Cl-2-pyridinyloxy)-Ph                        (2-CN--Ph)CH.sub.2                                                                    2,6-diMeO--Ph                                                                           3-(4-CF.sub.3 --PhO)--Ph                                                                4-(PhO)-c-hexyl                                   CF.sub.3 CH.sub.2                                                                     3-(2-CN--PhO)--Ph                                                                       3-(2-Me--PhO)--Ph                                                                       5-PhO-2-pyrimidinyl                               2-MeS--Ph                                                                             5-PhO-3-pyridinyl                                                                       5-PhO-2-pyridinyl                                                                       6-(2-NO.sub.2 --PhO)-4-pyrimidinyl                i-Bu    6-Me-2-pyridinyl                                                                        6-PhO-2-pyridinyl                                                                       6-(2-Cl--PhO)-4-pyrimidinyl                       2-CF.sub.3 O--Ph                                                                      3-CF.sub.3 O--Ph                                                                        6-CF.sub.3 -2-pyridinyl                                                                 6-(2-CF.sub.3 --PhO)4-pyrimidinyl                 4-Me--Ph                                                                              4-Br--Ph  6-PhO-3-pyridinyl                                                                       4,6-diMeO-2-pyrimidinyl                           4-Cl--Ph                                                                              3-Et--Ph  2-pyrimidinyl                                                                           4,6-diMe-2-pyrimidinyl                            3-Me--Ph                                                                              4-Et--Ph  4-pyrimidinyl                                                                           6-CF.sub.3 -4-pyrimidinyl                         3-CF.sub.3 --Ph                                                                       4-MeO--Ph 4-MeO-2-pyrimidinyl                                                                     4-CF.sub.3 -2-pyridinyl                           3-Cl-2-Me--Ph                                                                         4-t-Bu--Ph                                                                              4-Me-2-pyrimidinyl                                                                      4-CF.sub.3 -2-pyrimidinyl                         3-t-Bu--Ph                                                                            4-CN--Ph  6-MeO-4-pyrimidinyl                                                                     2-pyridinyl                                       3-NO.sub.2 --Ph                                                                       4-NO.sub.2 --Ph                                                                         2-Ph-4-thiazolyl                                                                        6-CF.sub.3 -2-pyrazinyl                           3-F--Ph 4-F--Ph   3-MeO-6-pyridazinyl                                                                     5-CF.sub.3 -3-pyridinyl                           4-CF.sub.3 --Ph                                                                       3-Ph--Ph  5-Me-2-furanyl                                                                          3-MeO-2-pyridinyl                                 3,4-diCl--Ph                                                                          3,4-diMe--Ph                                                                            2,5-diMe-3-thienyl                                                                      5-CN-2-pyridinyl                                  3,4-diCF.sub.3 --Ph                                                                   3,5,-diMe-Ph                                                                            3-OCF.sub.2 H--Ph                                                                       6-Me-2-pyridinyl                                  3-EtO--Ph                                                                             3-Mes--Ph 4-OCF.sub.2 2H--Ph                                          __________________________________________________________________________

                  TABLE 19                                                        ______________________________________                                        Compounds of Formula I wherein: A ═ N, G ═ N, W ═ O, X ═      MeO,                                                                          R.sup.2  ═ Me, R.sup.3  ═ R.sup.4  ═ H, the floating double       bond is attached to A, and                                                    Y ═ CH.sub.2 ON═C(H).                                                 Z         Z          Z           Z                                            ______________________________________                                        2-Me--Ph  3-Me--Ph   3-CF.sub.3 --Ph                                                                           3-Cl--Ph                                     4-Cl--Ph  4-CF.sub.3 --Ph                                                                          2,5-diMe--Ph                                                                              3,5-diCl--Ph                                 ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                        Compounds of Formula I wherein: A ═ N, G ═ N, W ═ O, X ═      MeO,                                                                          Z ═ 3-CF.sub.3 --Ph, R.sup.2  ═ Me, R.sup.3  ═ R.sup.4  ═     H, the floating                                                               double bond is attached to A, and                                             Y ═ CH.sub.2 ON═C(R.sup.7).                                           R.sup.7     R.sup.7     R.sup.7   R.sup.7                                     ______________________________________                                        CF.sub.3    OCH.sub.2 CF.sub.3                                                                        Et        n-Pr                                        Cl          MeO         EtO       MeS                                         ______________________________________                                    

                  TABLE 21                                                        ______________________________________                                        Compounds of Formula I wherein: A ═ O, G ═ C, W ═ O,              X ═ MeO, R.sup.3  ═ R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(R.    sup.7),                                                                       the floating double bond is attached to G, and                                R.sup.2  ═ Me                                                             R.sup.7                                                                              Z             R.sup.7  Z                                               ______________________________________                                        c-propyl                                                                             3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              c-propyl 3,4-(OCHFCF.sub.2 O)--Ph                        c-propyl                                                                             3,4-(OCF.sub.2 O)--Ph                                                                       c-propyl Ph                                              c-propyl                                                                             4-CF.sub.3 --Ph                                                                             c-propyl 3-CF.sub.3 --Ph                                 c-propyl                                                                             4-Cl--Ph      c-propyl 3-Cl--Ph                                        c-propyl                                                                             2-Me--Ph      c-propyl 3-OCF.sub.3 --Ph                                CF.sub.3                                                                             3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              CF.sub.3 3,4-(OCHFCF.sub.2 O)--Ph                        CF.sub.3                                                                             3,4-(OCF.sub.2 O)--Ph                                                                       CF.sub.3 Ph                                              CF.sub.3                                                                             4-CF.sub.3 --Ph                                                                             CF.sub.3 3-CF.sub.3 --Ph                                 CF.sub.3                                                                             4-Cl--Ph      CF.sub.3 3-Cl--Ph                                        CF.sub.3                                                                             2-Me--Ph      CF.sub.3 3-OCF.sub.3 --Ph                                Et     3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              Et       3,4-(OCHFCF.sub.2 O)--Ph                        Et     3,4-(OCF.sub.2 O)--Ph                                                                       Et       Ph                                              Et     4-CF.sub.3 --Ph                                                                             Et       3-CF.sub.3 --Ph                                 Et     4-Cl--Ph      Et       3-Cl--Ph                                        Et     2-Me--Ph      Et       3-OCF.sub.3 --Ph                                ______________________________________                                    

                  TABLE 22                                                        ______________________________________                                        Compounds of Formula I wherein: A ═ NMe, G ═ C, W ═ O,            X ═ MeO, R.sup.3  ═ R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(R.    sup.7),                                                                       the floating double bond is attached to G, and                                R.sup.2  ═ Me                                                             R.sup.7                                                                              Z             R.sup.7  Z                                               ______________________________________                                        c-propyl                                                                             3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              c-propyl 3,4-(OCHFCF.sub.2 O)--Ph                        c-propyl                                                                             3,4-(OCF.sub.2 O)--Ph                                                                       c-propyl Ph                                              c-propyl                                                                             4-CF.sub.3 --Ph                                                                             c-propyl 3-CF.sub.3 --Ph                                 c-propyl                                                                             4-Cl--Ph      c-propyl 3-Cl--Ph                                        c-propyl                                                                             2-Me--Ph      c-propyl 3-OCF.sub.3 --Ph                                CF.sub.3                                                                             3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              CF.sub.3 3,4-(OCHFCF.sub.2 O)--Ph                        CF.sub.3                                                                             3,4-(OCF.sub.2 O)--Ph                                                                       CF.sub.3 Ph                                              CF.sub.3                                                                             4-CF.sub.3 --Ph                                                                             CF.sub.3 3-CF.sub.3 --Ph                                 CF.sub.3                                                                             4-Cl--Ph      CF.sub.3 3-Cl--Ph                                        CF.sub.3                                                                             2-Me--Ph      CF.sub.3 3-OCF.sub.3 --Ph                                Et     3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              Et       3,4-(OCHFCF.sub.2 O)--Ph                        Et     3,4-(OCF.sub.2 O)--Ph                                                                       Et       Ph                                              Et     4-CF.sub.3 --Ph                                                                             Et       3-CF.sub.3 --Ph                                 Et     4-Cl--Ph      Et       3-Cl--Ph                                        Et     2-Me--Ph      Et       3-OCF.sub.3 --Ph                                ______________________________________                                    

                  TABLE 23                                                        ______________________________________                                        Compounds of Formula I wherein: A ═ N, G ═ N, W ═ O,              X ═ MeO, R.sup.3  ═ R.sup.4  ═ H, Y ═ CH.sub.2 ON═C(R.    sup.7),                                                                       the floating double bond is attached to G, and                                R.sup.2  ═ Me                                                             R.sup.7                                                                              Z             R.sup.7  Z                                               ______________________________________                                        c-propyl                                                                             3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              c-propyl 3,4-(OCHFCF.sub.2 O)--Ph                        c-propyl                                                                             3,4-(OCF.sub.2 O)--Ph                                                                       c-propyl Ph                                              c-propyl                                                                             4-CF.sub.3 --Ph                                                                             c-propyl 3-CF.sub.3 --Ph                                 c-propyl                                                                             4-Cl--Ph      c-propyl 3-Cl--Ph                                        c-propyl                                                                             2-Me--Ph      c-propyl 3-OCF.sub.3 --Ph                                CF.sub.3                                                                             3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              CF.sub.3 3,4-(OCHFCF.sub.2 O)--Ph                        CF.sub.3                                                                             3,4-(OCF.sub.2 O)--Ph                                                                       CF.sub.3 Ph                                              CF.sub.3                                                                             4-CF.sub.3 --Ph                                                                             CF.sub.3 3-CF.sub.3 --Ph                                 CF.sub.3                                                                             4-Cl--Ph      CF.sub.3 3-Cl--Ph                                        CF.sub.3                                                                             2-Me--Ph      CF.sub.3 3-OCF.sub.3 --Ph                                Et     3,4-(OCH.sub.2 CH.sub.2 O)--Ph                                                              Et       3,4-(OCHFCF.sub.2 O)--Ph                        Et     3,4-(OCF.sub.2 O)--Ph                                                                       Et       Ph                                              Et     4-CF.sub.3 --Ph                                                                             Et       3-CF.sub.3 --Ph                                 Et     4-Cl--Ph      Et       3-Cl--Ph                                        Et     2-Me--Ph      Et       3-OCF.sub.3 --Ph                                ______________________________________                                    

                  TABLE 24                                                        ______________________________________                                        Compounds of Formula I wherein: A = O, G = C, W = O, X = MeO,                 R.sup.3 = R.sup.4 = H, the floating double bond is attached to G, and         R.sup.2 = Me                                                                  Y--Z                                                                          ______________________________________                                         ##STR48##                                                                     ##STR49##                                                                     ##STR50##                                                                     ##STR51##                                                                     ##STR52##                                                                     ##STR53##                                                                     ##STR54##                                                                     ##STR55##                                                                     ##STR56##                                                                    ______________________________________                                    

                  TABLE 25                                                        ______________________________________                                        Compounds of Formula I wherein: A = NMe, G = C, W = O, X = MeO,               R.sup.3 = R.sup.4 = H, the floating double bond is attached to G, and         R.sup.2 = Me                                                                  Y--Z                                                                          ______________________________________                                         ##STR57##                                                                     ##STR58##                                                                     ##STR59##                                                                     ##STR60##                                                                     ##STR61##                                                                     ##STR62##                                                                     ##STR63##                                                                     ##STR64##                                                                     ##STR65##                                                                    ______________________________________                                         }{0561

                  TABLE 26                                                        ______________________________________                                        Compounds of Formula I wherein: A = N, G = N, W = O, X = MeO,                 R.sup.3 = R.sup.4 = H, the floating double bond is attached to A, and         R.sup.2 = Me                                                                  Y--Z                                                                          ______________________________________                                         ##STR66##                                                                     ##STR67##                                                                     ##STR68##                                                                     ##STR69##                                                                     ##STR70##                                                                     ##STR71##                                                                     ##STR72##                                                                     ##STR73##                                                                     ##STR74##                                                                    ______________________________________                                    

Formulation/Utility

Compounds of this invention will generally be used in formulation withan agriculturally suitable composition. The fungicidal compositions ofthe present invention comprise an effective amount of at least onecompound of Formula I as defined above and at least one of (a) asurfactant, (b) an organic solvent, and (c) at least one solid or liquiddiluent. Useful formulations can be prepared in conventional ways. Theyinclude dusts, granules, pellets, solutions, suspensions, emulsions,wettable powders, emulsifiable concentrates, dry flowables and the like.Sprayable formulations can be extended in suitable media and used atspray volumes from about one to several hundred liters per hectare. Highstrength compositions are primarily used as intermediates for furtherformulation. The formulations will typically contain effective amountsof active ingredient, diluent and surfactant within the followingapproximate ranges which add up to 100 weight percent.

    ______________________________________                                                        Weight Percent                                                                Active                                                                        Ingredient                                                                           Diluent  Surfactant                                    ______________________________________                                        Wettable Powders    5-90    0-74    1-10                                      Oil Suspensions, Emulsions,                                                                       5-50   40-95    0-15                                      Solutions, (including Emulsifiable                                            Concentrates)                                                                 Dusts               1-25   70-99    0-5                                       Granules, Baits and Pellets                                                                     0.01-99   5-99.99 0-15                                      High Strength Compositions                                                                        90-99   0-10    0-2                                       ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents and solvents are described inMarsden, Solvents Guide, 2nd Ed., Interscience, New York, (1950).McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp.,Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of SurfaceActive Agents, Chemical Publ. Co., Inc., New York, (1964), listsurfactants and recommended uses. All formulations can contain minoramounts of additives to reduce foam, caking, corrosion, microbiologicalgrowth, and the like.

Methods for formulating such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer mill or fluidenergy mill. Water-dispersible granules can be produced by agglomeratinga fine powder composition; see for example, Cross et al., PesticideFormulations, Washington, D.C., (1988), pp 251-259. Suspensions areprepared by wet-milling; see, for example U.S. Pat. No. 3,060,084.Granules and pellets can be made by spraying the active material uponpreformed granular carriers or by agglomeration techniques. SeeBrowning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp147-148, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, NewYork, (1963), pp 8-57 and following, and WO 91/13546. Pellets can beprepared as described in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in DE 3,246,493.

For further information regarding the art of formulation, see U.S. Pat.No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10through 41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7,line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as aScience, John Wiley and Sons, Inc., New York, (1961), pp 81-96; andHance et al., Weed Control Handbook, 8th Ed., Blackwell ScientificPublications, Oxford, (1989).

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound 1 refers to thecompound in Index Table A hereinafter.

    ______________________________________                                        Example A                                                                     Wettable Powder                                                               Compound 1                65.0%                                               dodecylphenol polyethylene glycol ether                                                                  2.0%                                               sodium ligninsulfonate     4.0%                                               sodium silicoaluminate     6.0%                                               montmorillonite (calcined)                                                                              23.0%.                                              Example B                                                                     Granule                                                                       Compound 1                10.0%                                               attapulgite granules (low volative                                                                      90.0%.                                              matter, 0.71/0.30 mm; U.S.S. No.                                              25-50 sieves)                                                                 Example C                                                                     Extruded Pellet                                                               Compound 1                25.0%                                               anhydrous sodium sulfate  10.0%                                               crude calcium ligninsulfonate                                                                            5.0%                                               sodium alkylnaphthalenesulfonate                                                                         1.0%                                               calcium/magnesium bentonite                                                                             59.0%.                                              Example D                                                                     Emulsifiable Concentrate                                                      Compound 1                20.0%                                               blend of oil soluble sulfonates                                                                         10.0%                                               and polyoxyethylene ethers                                                    isophorone                70.0%.                                              ______________________________________                                    

The compounds of this invention are useful as plant disease controlagents. The present invention therefore further comprises a method forcontrolling plant diseases caused by fungal plant pathogens comprisingapplying to the plant or portion thereof, or to the plant seed orseedling, an effective amount of a compound of Formula I or a fungicidalcomposition containing said compound. The compounds and compositions ofthis invention provide control of diseases caused by a broad spectrum offungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete andDeuteromycete classes. They are effective in controlling a broadspectrum of plant diseases, particularly foliar pathogens of ornamental,vegetable, field, cereal, and fruit crops. These pathogens includePlasmopara viticola, Phytophthora infestans, Peronospora tabacina,Pseudoperonospora cubensis, Pythium aphanidermatum, Alternariabrassicae, Septoria nodorum, Cercosporidium personatum, Cercosporaarachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola,Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaeraleucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur,Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinastriiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerothecafuliginea, Fusarium oxysporum, Verticillium dahliae, Pythiumaphanidermatum, Phytophthora megasperma and other generea and speciesclosely related to these pathogens.

Compounds of this invention can also be mixed with one or more otherinsecticides, fungicides, nematocides, bactericides, acaricides,semiochemicals, repellants, attractants, pheromones, feeding stimulantsor other biologically active compounds to form a multi-componentpesticide giving an even broader spectrum of agricultural protection.Examples of other agricultural protectants with which compounds of thisinvention can be formulated are: insecticides such as acephate,avermectin B, azinphosmethyl, bifenthrin, biphenate, buprofezin,carbofuran, chlordimeform, chlorpyrifos, cyfluthrin, deltamethrin,diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin,fenvalerate, fipronil, flucythrinate, flufenprox, fluvalinate, fonophos,isofenphos, malathion, metaldehyde, metha-midophos, methidathion,methomyl, methoprene, methoxychlor, monocrotophos, oxamyl,parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon,pirimicarb, profenofos, rotenone, sulprofos, terbufos,tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon andtriflumuron; fungicides such as benomyl, blasticidin S, bromuconazole,captafol, captan, carbendazim, chloroneb, chlorothalonil, copperoxychloride, copper salts, cymoxanil, cyproconazole, dichloran,diclobutrazol, diclomezine, difenoconazole, diniconazole, dodine,edifenphos, epoxyconazole fenarimol, fenbuconazole, fenpropidine,fenpropimorph, fluquinconazole, flusilazol, flutolanil, flutriafol,folpet, furalaxyl, hexaconazole, ipconazole, ipobenfos, iprodione,isoprothiolane, kasugamycin, mancozeb, maneb, mepronil, metalaxyl,metconazole, myclobutanil, neo-asozin, oxadixyl, penconazole,pencycuron, phosethyl-Al, probenazole, prochloraz, propiconazole,pyrifenox, pyroquilon, sulfur, tebuconazole, tetraconazole,thiabendazole, thiophanate-methyl, thiuram, triadimefon, triadimenol,tricyclazole, uniconzole, validamycin and vinclozolin; nematocides suchas aldoxycarb, fenamiphos and fosthietan; bactericides such asoxytetracyline, streptomycin and tribasic copper sulfate; acaricidessuch as amitraz, binapacryl, chlorobenzilate, cyhexatin, dicofol,dienochlor, fenbutatin oxide, hexythiazox, oxythioquinox, propargite andtebufenpyrad; and biological agents such as Bacillus thuringiensis andbaculovirus.

In certain instances, combinations with other fungicides having asimiliar spectrum of control but a different mode of action will beparticularly advantageous for resistance management.

Plant disease control is ordinarily accomplished by applying aneffective amount of a compound of this invention either pre- orpost-infection, to the portion of the plant to be protected such as theroots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media(soil or sand) in which the plants to be protected are growing. Thecompounds can also be applied to the seed to protect the seed andseedling.

Rates of application for these compounds can be influenced by manyfactors of the environment and should be determined under actual useconditions. Foliage can normally be protected when treated as a rate offrom less than 1 g/ha to 5,000 g/ha of active ingredient. Seed andseedlings can normally be protected when seed is treated at a rate offrom 0.1 to 10 g per kilogram of seed.

The following TESTS demonstrate the control efficacy of compounds ofthis invention on specific pathogens. The pathogen control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A-D for compound descriptions.

Test compounds were first dissolved in acetone in an amount equal to 3%of the final volume and then suspended at a concentration of 200 ppm inpurified water containing 250 ppm of the surfactant Trem® 014(polyhydric alcohol esters). The resulting test suspensions were thenused in the following tests.

TEST A

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporedust of Erysiphe graminis f. sp. tritici, (the causal agent of wheatpowdery mildew) and incubated in a growth chamber at 20° C. for 7 days,after which disease ratings were made.

TEST B

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Puccinia recondita (the causal agent of wheat leaf rust)and incubated in a saturated atmosphere at 20° C. for 24 h, and thenmoved to a growth chamber at 20° C. for 6 days, after which diseaseratings were made.

TEST C

The test suspension was sprayed to the point of run-off on riceseedlings. The following day the seedlings were inoculated with a sporesuspension of Pyricularia oryzae (the causal agent of rice blast) andincubated in a saturated atmosphere at 27° C. for 24 h, and then movedto a growth chamber at 30° C. for 5 days, after which disease ratingswere made.

TEST D

The test suspension was sprayed to the point of run-off on tomatoseedlings. The following day the seedlings were inoculated with a sporesuspension of Phytophthora infestans (the causal agent of potato andtomato late blight) and incubated in a saturated atmosphere at 20° C.for 24 h, and then moved to a growth chamber at 20° C. for 5 days, afterwhich disease ratings were made.

TEST E

The test suspension was sprayed to the point of run-off on grapeseedlings. The following day the seedlings were inoculated with a sporesuspension of Plasmopara viticola (the causal agent of grape downymildew) and incubated in a saturated atmosphere at 20° C. for 24 h,moved to a growth chamber at 20° C. for 6 days, and then incubated in asaturated atmosphere at 20° C. for 24 h, after which disease ratingswere made.

The test suspension was sprayed to the point of run-off on cucumberseedlings. The following day the seedlings were inoculated with a sporesuspension of Botrytis cinerea (the causal agent of gray mold on manycrops) and incubated in a saturated atmosphere at 20° C. for 48 h, andmoved to a growth chamber at 20° C. for 5 days, after which diseaseratings were made.

    ______________________________________                                        INDEX TABLE A                                                                 Compound                    m.p. (° C.)                                ______________________________________                                                    ##STR75##       117-120                                           ______________________________________                                    

    ______________________________________                                        INDEX TABLE B                                                                  ##STR76##                                                                    Compound    Y         Z         m.p. (° C.)                            ______________________________________                                        2           O         2-MeO--Ph oil*                                          3           O         CH.sub.2 --Ph                                                                           oil*                                          4           --        Me        oil*                                          5           CH.sub.2 O                                                                              2-MeO--Ph oil*                                          ______________________________________                                         *See Index Table D for .sup.1 H NMR data.                                

    __________________________________________________________________________    INDEX TABLE C                                                                  ##STR77##                                                                    Compound                                                                            W X      Y       Z          m.p. (° C.)                          __________________________________________________________________________    6     O MeS    O       Ph         129-13                                      7     O MeO    O       Me         123--12                                     8     O MeO    --      Me         95-97                                       9     O MeS    --      Me         95-97                                       10    O Cl     --      Me         99-104                                      11    O MeO    O       Ph         88-91                                       12    O Cl     CH.sub.2 O                                                                            2-Me--Ph   88-96                                       13    O MeO    CH.sub.2 O                                                                            2-Me--Ph   110-1                                       14    O EtO    CH.sub.2 O                                                                            2-Me--Ph   oil*                                        15    O MeS    CH.sub.2 O                                                                            2-Me--Ph   80-88                                       16    O OCH.sub.2 C.tbd.CH                                                                   CH.sub.2 O                                                                            2-Me--Ph   122--1                                      17    O Cl     CH.sub.2 ON═C(Me)                                                                 4-Me--Ph   oil*                                        18    O MeO    CH.sub.2 ON═C(Me)                                                                 4-Me--Ph   116-1                                       19    O MeS    CH.sub.2 ON═C(Me)                                                                 4-Me--Ph   oil*                                        20    O Cl                                                                                    ##STR78##         oil*                                        21    S MeS    O       Ph         oil*                                        22    O MeO                                                                                   ##STR79##         126-1                                       23    O Cl     CH.sub.2 ON═C(H)                                                                  Ph         oil*                                        24    O MeS                                                                                   ##STR80##         oil*                                        25    O Cl     CH.sub.2 O                                                                            3-(OPh)--Ph                                                                              oil*                                        26    O      MeO                                                                                CH.sub.2 O                                                                              3-(OPh)--Ph                                                                                 oil*                                27    O      MeO                                                                                CH.sub.2 ON═C(H)                                                                  Ph                101-104                           28    O      MeS                                                                                CH.sub.2 O                                                                              3-(OPh)--Ph                                                                                 95-100                              29    O      Cl                                                                                  CH.sub.2 S                                                                             2-Me--Ph                                                                                     106-109                            30    O      MeO                                                                                CH.sub.2 S                                                                              2-Me--Ph                                                                                     115-118                            31    O      MeS                                                                                CH.sub.2 S                                                                              2-Me--Ph                                                                                     82-86                              32    O      Cl                                                                                  CH.sub.2 S                                                                             2-benzthiazolyl                                                                             95-97                               33    O      MeO                                                                                C.tbd.C                                                                                 Ph              164-166                           34    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 4-Br--Ph                                                                                       115-120                            35    O      Cl                                                                                  CH.sub.2 ON═C(Me)                                                                4-Br--Ph                                                                                       gum*                               36    O      Cl                                                                                  CH.sub.2 O                                                                             3-(benzoyl)-Ph                                                                              oil*                                37    O      MeS                                                                                CH.sub.2 ON═C(Me)                                                                 4-Br--Ph                                                                                       117-122                            38    O      MeO                                                                                CH.sub.2 O                                                                              3-(benzoyl)-Ph                                                                              oil*                                39    O      Cl                                                                                  CH═NOCH.sub.2                                                                      4-Cl--Ph                                                                                     oil*                               40    O      Cl                                                                                  CH.sub.2 ON═C(Me)                                                                 1,3-benzodixol-5-yl                                                                          oil*                                41    O      MeO                                                                                CH═NOCH.sub.2                                                                      4-Cl--Ph                                                                                      oil*                               42    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 1,3-benzodixol-5-yl                                                                           oil*                                43    O      Cl                                                                                  O        (6-OPh)-4-pyrimidinyl                                                                      oil*                                 44    O      MeO                                                                                CH.sub.2 S                                                                              2-benzthiazolyl                                                                             95-97                               45    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 2-Me--Ph                                                                                       oil*                               46    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 4-CF.sub.3 --Ph                                                                               138-144                             47    O      MeO                                                                                CH.sub.2 ON═C(CF.sub.3)                                                          Ph                 oil*                              48    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 Ph                oil*                              49    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 3-Me--Ph                                                                                       oil*                               50    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                  4-MeO--Ph                                                                                     oil*                               51    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 3-Cl--Ph                                                                                       oil*                               52    O      MeO                                                                                CH.sub.2 ON═C(Me)                                                                 Ph                oil*                              53    O      MeO                                                                                  CH═NOCH.sub.2                                                                    2-Me--Ph                                           __________________________________________________________________________                                      oil*                                         *See Index Table D for .sup.1 H NMR data.                                

                                      INDEX TABLE D                               __________________________________________________________________________    Cmpd No.                                                                           .sup.1 H NMR Data (200 MHz, CDCl.sub.3  solution)                        __________________________________________________________________________    2    δ7.51(dd, 1H), 7.27(dt, 1H), 7.17(m, 2H), 6.97(dd, 1h), 6.6(m,          3H), 3.92(s, 3H),                                                             3.74(s, 3H), 3.33(s, 3H)                                                 3    δ7.32(m, 7H), 6.99(m, 2H), 5.08(s, 2H), 3.84(s, 3H), 3.42(s,            3H)                                                                      4    δ7.25(m, 4H), 3.93(s, 3H), 3.45(s, 3H), 2.30(s, 3H)                5    δ7.61(d, 1H), 7.35(m, 3H), 7.11(m, 2H), 6.84(t, 2H), 5.12(s,            2H), 3.96(s, 3H),                                                             3.415(s, 3H), 2.24(s, 3H)                                                14   δ7.65(d, 1H), 7.45(m, 2H), 7.23(m, 1H), 7.10(m, 2H), 6.82(t,            1H), 6.78(d, 1H),                                                             5.08(s, 2H), 4.29(m, 2H), 3.41(s, 3H), 2.24(s, 3H), 1.31(t, 3H)          17   δ7.6-7.45(m, 5H), 7.20(m, 1H), 7.14(d, 2H), 5.27(d, 1H),                5.16(d, 1H),                                                                  3.46(s, 3H), 2.34(s, 3H), 2.16(s, 3H)                                    19   δ7.6(d, 1H), 7.5(m, 3H), 7.4(t, 1H), 7.25(m, 1H), 7.15(d, 2H),          5.26(d, 1H),                                                                  5.20(d, 1H), 3.48(s, 3H), 2.41(s, 3H), 2.43(s, 3H), 2.18(s, 3H)          20   δ7.62(m, 2H), 7.5(m, 2H), 7.35-7.2(m, 4H), 5.25(d, 1H),                 5.15(d, 1H),                                                                  3.48(s, 3H), 3.02(m, 2H), 2.85(m, 2H)                                    21   δ7.42(m, 2H), 7.10(m, 1H), 7.06(m, 3H), 6.99(t, 1H), 6.68(d,            2H), 3.37(s, 3H),                                                             2.51(s, 3H)                                                              23   δ8.01(s, 1H), 7.61(d, 1H), 7.52(m, 4H), 7.35(m, 3H), 7.25(d,            1H), 5.23(d, 1H),                                                             5.15(d, 1H), 3.49(s, 3H)                                                 24   δ7.6(m, 2H), 7.5-7.4(m, 3H), 7.3-7.2(m, 3H), 5.24(d, 1H),               5.20(d, 1H),                                                                  3.48(s, 3H), 2.40(s, 3H)                                                 25   δ7.6-7.4(m, 4H), 7.35(m, 2H), 7.2(m, 2H), 7.0(d, 2H), 6.6(m,            3H), 5.04(d, 1H),                                                             5.00(d, 1H), 3.45(s, 3H)                                                 26   δ7.6(d, 1H), 7.45(m, 2H), 7.33(t, 2H), 7.19(m, 2H), 7.10(t,             1H), 7.01(d, 2H),                                                             6.6(m, 3H), 5.03(m, 2H), 3.87(s, 3H), 3.39(s, 3H)                        35   δ7.6-7.4(m, 7H), 7.23(d, 1H), 5.28(d, 1H), 5.17(d, 1H),                 3.46(s, 3H), 2.14(s, 3H)                                                 36   δ7.80(d, 2H), 7.65-7.45(m, 6H), 7.36(d, 2H), 7.30(m, 1H),               7.25(m, 1H),                                                                  7.10(t, 1H), 5.15(d, 1H), 5.10(d, 1H), 3.45(s, 2H)                       38   δ7.77(d, 2H), 7.6(m, 2H), 7.47(m, 4H), 7.35(m, 3H), 7.25(m,             1H), 7.10(m, 1H),                                                             5.13(d, 1H), 5.12(d, 1H), 3.89(s, 3H), 3.38(s, 3H)                       39   δ8.03(s, 1H), 7.70(d, 1H), 7.53(m, 2H), 7.35-7.25(m, 5H),               5.06(s, 2H),                                                                  3.46(s, 3H)                                                              40   δ7.6-7.5(m, 3H), 7.24(m, 1H), 7.13(s, 1H), 7.02(d, 1H),                 6.78(d, 1H), 5.96(s, 2H),                                                     5.26(d, 1H), 5.14(d, 1H), 3.48(s, 3H), 2.13(s, 3H)                       41   δ8.04(s, 1H), 7.8(m, 1H), 7.45(m, 2H)7.35-7.25(m, 5H), 5.10(s,          2H), 3.86(s, 3H                                                               3.41(s, 3H)                                                              42   δ7.58(m, 1H), 7.43(m, 2H), 7.25(m, 1H), 7.15(m, 1H), 7.02(d,            1H), 6.76(d, 1H),                                                             5.96(s, 2H), 5.22(d, 1H), 5.18(d, 1H)3.89(s, 3H), 3.42(s, 3H),                2.15(s, 3H)                                                              43   δ8.40(s, 1H), 7.6(m, 1H), 7.5-7.4(m, 5H), 7.3(d, 1H), 7.18(m,           2H), 6.38(s, 1H),                                                             3.45(s, 3H)                                                              45   δ7.55(d, 1H), 7.40(m, 3H), 7.20(m, 4H), 5.21(d, 1H), 3.87(s,            3H), 3.42(s, 3H),                                                             2.24(s, 3H)                                                              47   δ7.6-7.2(m, 9H), 5.4-5.2(m, 2H), 3.87, 3.83(s, 3H), 3.41,               3.40(s, 3H)                                                              48   δ7.6(m, 3H), 7.44(m, 2H), 7.35(m, 3H), 7.25(m, 1H), 5.26(d,             1H), 5.22(d, 1H),                                                             3.88(s, 3H), 3.49(s, 3H), 2.20(s, 3H)                                    49   δ7.5(d, 1H), 7.40(m, 4H), 7.23(m, 2H), 7.18(d, 1H), 5.26(d,             1H), 5.21(d, 1H),                                                             3.88(s, 3H)3.41(s, 3H), 2.36(s, 3H), 2.19(s, 3H)                         50   δ7.56(m, 3H), 7.45(m, 2H), 7.25(m, 1H), 6.86(d, 2H), 5.24(d,            1H), 5.19(d, 1H),                                                             3.88(s, 3H), 3.81(s, 3H), 3, 41(s, 3H), 2.17(s, 3H)                      51   δ7.5(m, 2H), 7.45(m, 3H), 7.3(m, 3H), 5.27(d, 1H), 5.22(d,              1H), 389(s, 3H)                                                          52   δ8.02, 8.01(s, 1H), 7.8, 7.7(m, 1H), 7.45(m, 2H), 7.35(m, 4H),          7.25(m, 2H), 5.25                                                             (m, 1H), 3.88, 3.74(s, 3H), 3.45, 3.39(s, 3H), 1.62-1.56(m, 3H)          53   δ8.04(s, 1H), 7.81(m, 1H), 7.45(m, 2H), 7.38-7.18(m, 5H),               5.18(s, 2H),                                                                  3.86(s, 3H), 3.42(s, 3H), 2.38(s, 3H)                                    __________________________________________________________________________

Results for Tests A-F are given in Table 1. In the table, a rating of100 indicates 100% disease control and a rating of 0 indicates nodisease control (relative to the controls).

                  TABLE 1                                                         ______________________________________                                                Test    Test    Test  Test  Test  Test                                Cmpd No.                                                                              A       B       C     D     E     F                                   ______________________________________                                        1       57      79      0     0     17    68                                  2       86      93      0     0     100   0                                   3       57      79      0     61    100   68                                  4       0       0       0     0     100   0                                   5       99      100     0     46    100   43                                  6       98      100     36    85    100   42                                  7       73      9       0     33    5     3                                   8       0       0       0     0     35    46                                  9       0       0       0     0     35    0                                   10      35      3       0     43    78    0                                   11      100     100     0     64    100   50                                  12      95      97      0     47    92    71                                  13      98      100     0     0     69*   63                                  14      78      81      0     0     0     0                                   15      100     100     0     63    100   36                                  16      92      57      0     0     0     0                                   17*     78      91      0     0     36    44                                  18      52      0       0     0     0     0                                   19      0       0       0     0     0     62                                  20      63      84      0     26    99    65                                  21      --      --      0     --    --    --                                  22      38      100     0     47    100   47                                  23      38      89      0     0     100   0                                   24      0       98      97    47    100   70                                  25      0       84      88    16    100   0                                   26      72      100     0     73    100   44                                  27      72      93      0     16    100   2                                   28      83      97      19    59    100   0                                   29      16      97      0     25    8     0                                   30      95      96      0     47    100   47                                  31      89      99      0     46    100   0                                   32      60      53      0     0     100   47                                  33      95      98      0     77    100   0                                   34      90      100     88    64    100   0                                   35      0       97      0     0     99    9                                   36      63      93      62    46    100   0                                   37      98      100     93    63    100   48                                  38      0       99      73    26    100   0                                   39      32      85      73    0     45    0                                   40      59      97      93    0     76    49                                  41      97      100     0     0     100   0                                   42      92      100     62    64    100   68                                  43      97      99      50    26    97    0                                   44      73      100     0     47    100   69                                  45      94      100     0     0     100   47                                  46      100     100     100   93    100   0                                   47      96      100     0     0     100   0                                   48      100     100     0     47    100   0                                   49      100     100     88    86    100   47                                  50      92      100     97    77    --    45                                  51      100     100     100   97    --    89                                  ______________________________________                                         *Tested at 40 ppm.                                                       

What is claimed is:
 1. A compound selected from Formula I, andagriculturally suitable salts thereof, ##STR81## wherein: A is N;G is Nand the floating double bond is attached to A; W is O or S; X is OR¹ ;S(O)_(m) R¹ ; or halogen; R¹ is C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆cycloalkyl; C₂ -C₄ alkylcarbonyl, C₂ -C₄ alkoxycarbonyl; or benzoyloptionally substituted with R¹³ ; R² is H; C₁ -C₆ alkyl; C₁ -C₆haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl, C₂ -C₄alkoxycarbonyl; or benzoyl optionally substituted with R¹³ ; R³ and R⁴are each independently H; halogen; cyano; nitro; C₁ -C₆ alkyl; C₁ -C₆haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆haloalkynyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆ alkenyloxy; or C₂-C₆ alkynyloxy; Y is --O--; --S(O)_(n) --; --CHR⁶ CHR⁶ --; --CR⁶ ═CR⁶--; --C.tbd.C--; --CHR⁶ O--; --OCHR⁶ --; --CHR⁶ S(O)_(n) --; --S(O)_(n)CHR⁶ --; --CHR⁶ O--N═C(R⁷)--; --(R⁷)C═N--OCH(R⁶)--; --C(R⁷)═N--O--;--O--N═C(R⁷)--; --CHR⁶ OC(═O)N(R¹⁵)--; or a direct bond; and thedirectionality of the Y linkage is defined such that the moiety depictedon the left side of the linkage is bonded to the phenyl ring and themoiety on the right side of the linkage is bonded to Z; R⁶ isindependently H or C₁ -C₃ alkyl; R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂-C₄ alkylcarbonyl; C₂ -C₄ alkoxycarbonyl; cyano; or morpholinyl; Z is a6-membered nonaromatic heterocyclic ring system or Z is a 6-memberedaromatic heterocyclic ring system, each nonaromatic or aromatic ringsystem containing 1 to 5 heteroatoms independently selected from thegroup 1-4 nitrogen, 1-2 oxygen, and 1-2 sulfur, each nonaromatic oraromatic ring system optionally substituted with one of R⁹, R¹⁰, or bothR⁹ and R¹⁰ ; R⁹ is 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₁ -C₆ alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl;C₁ -C₆ alkylsulfonyl; C₃ -C₆ cycloalkyl; C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆alkyl); NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ; --C(R¹⁸)═NOR¹⁷ ; cyano; ornitro; or R⁹ is phenyl, benzyl, benzoyl, phenoxy, pyridinyl,pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, orpyrimidinyloxy each optionally substituted with one of R¹¹, R¹², or bothR¹¹ and R¹² ; R¹⁰ is halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁ -C₄alkoxy; nitro; or cyano; or R⁹ and R¹⁰, when attached to adjacent atoms,are taken together as --OCH₂ O-- or --OCH₂ CH₂ O--; each CH₂ groupoptionally substituted with 1-2 halogens; R¹¹ and R¹² are eachindependently halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁ -C₄ alkoxy; C₁-C₄ haloalkoxy; nitro; or cyano; each R¹³ is halogen; C₁ -C₃ alkyl; C₁-C₃ haloalkyl; C₁ -C₃ alkoxy; C₁ -C₃ haloalkoxy; nitro; or cyano; R¹⁵,R¹⁷, and R¹⁸ are each independently H; C₁ -C₃ alkyl; or phenyloptionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano; and m and n and are eachindependently 0, 1 or
 2. 2. A compound of claim 1 whereinW is O; R¹ isC₁ -C₃ alkyl or C₁ -C₃ haloalkyl; R² is H; C₁ -C₆ alkyl; C₁ -C₆haloalkyl; or C₃ -C₆ cycloalkyl; R³ and R⁴ are each independently H;halogen; cyano; nitro; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; orC₁ -C₆ haloalkoxy; Y is --O--; --CH═CH--; --CH₂ O--; --OCH₂ --; --CH₂S(O)_(n) --; --CH₂ O--N═C(R⁷)--; --C(R⁷)═C--O--; --CH₂ OC(O)NH--; or adirect bond; R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂-C₆ alkynyl; or cyano; Z is ##STR82## each group optionally substitutedwith one R⁹, R¹⁰, or both R⁹ and R¹⁰ ; R⁹ is 1-2 halogen; C₁ -C₆ alkyl;C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆ alkylthio;cyano; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆ alkyl); C₃ -C₆ cycloalkyl; r N(C₁-C₆ alkyl)₂ ; or R⁹ is phenyl, phenoxy, pyridinyl, pyridinyloxy,pyrimidinyl, or pyrimidinyloxy each optionally substituted with one ofR¹¹, R¹², or both R¹¹ and R¹² ; and R¹⁹ is H; C₁ -C₆ alkyl; C₁ -C₆haloalkyl; or phenyl optionally substituted with halogen, C₁ -C₄ alkyl,C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano.
 3. Acompound of claim 2 wherein Z is Z-16 to Z-21, each optionallysubstituted with one of R⁹, R¹⁰, or both R⁹ and R¹⁰.
 4. A compound ofclaim 3 whereinX is OR¹ ; R¹ is C₁ -C₃ alkyl; R² is H or C₁ -C₂ alkyl;R³ and R⁴ are each H; Y is --O--; --CH═CH--; --CH₂ O--; --OCH₂ --; --CH₂O--N═C(R⁷)--; or --CH₂ OC(═O)NH--; R⁷ is H; C₁ -C₃ alkyl; or C₁ -C₃haloalkyl; and Z is pyridinyl or pyrimidinyl, each optionallysubstituted with one of R⁹, R¹⁰, or both R⁹ and R¹⁰.
 5. A compound ofclaim 4 whereinY is --O--; --CH₂ O--; --OCH₂ --; or --CH₂ O--N═C(R⁷)--;and R⁷ is H; C₁ -C₂ alkyl; or C₁ -C₂ haloalkyl.
 6. A fungicidalcomposition comprising an effective amount of a compound of claim 1 andat least one component selected from the group consisting ofsurfactants, organic solvents, solid diluents and liquid diluents.
 7. Afungicidal composition of claim 6 which is selected from wettablepowders which contain from 5 to 90 weight percent active ingredient,from 0 to 74 weight percent diluent and from 1 to 10 weight percentsurfactant.
 8. A fungicidal composition of claim 6 which is selectedfrom oil suspensions, emulsions and solutions which contain from 5 to 50weight percent active ingredient, from 40 to 95 weight percent diluentand from 0 to 15 weight percent surfactant.
 9. A fungicidal compositionof claim 6 which is selected from dusts which contain from 1 to 25weight percent active ingredient, from 70 to 99 weight percent diluentand from 0 to 5 weight percent surfactant.
 10. A fungicidal compositionof claim 6 which is selected from granules, baits and pellets whichcontain from 0.01 to 99 weight percent active ingredient, from 5 to99.99 weight percent diluent and from 0 to 15 weight percent surfactant.11. A fungicidal composition of claim 6 which is selected from highstrength compositions which contain from 90 to 99 weight percent activeingredient, from 0 to 10 weight percent diluent and from 0 to 2 weightpercent surfactant.
 12. A method for controlling plant diseases causedby fungal plant pathogens comprising applying to the plant or portionthereof, or to the plant seed or seedling, an effective amount of acompound of claim 1.